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Asymmetric synthesis

     Dr. Shaikh A. R
• Asymmetric catalytic reduction:
Asymmetric catalytic reduction is the use of various chiral catalysts to
   reduce a pro-chiral organic compound to obtain a chiral product. This is
   one of the several techniques used in chiral synthesis.
e.g.                       H (g)
                O   O
                                2
                                                      OH   O
                              RuCl2 [(R)-BINAP]
            R           OMe
                               MeOH               R            OMe



    BINAP=2,2'-bis(diphenylphosphino)-1,1'-binaphthyl


The Noyori asymmetric hydrogenation is a chemical reaction described as an
asymmetric reduction of β-keto esters.
Example in drug synthesis: Synthesis of Naproxen
Synthesis of Naproxen:
• Asymmetric catalytic oxidation:
• Is a technique of oxidising various substrate to give an
  enantiopure product using a catalyst.
• Reactions:
• Jacobsen epoxidation of alkenes using manganese-
  salen complex and NaOCl
• Sharpless epoxidation of allyl alcohols using
  titanium isopropoxide, diethyl tartrate, and
  t-butyl hydroxyperoxide
• Sharpless asymmetric dihydroxylation of alkenes using
  dihydroquinine or dihydroquinidine ligands on an
  osmium metal center
• Shi epoxidation of alkenes using oxone and a fructose-
  derived chiral catalyst
• Sulfonyloxaziridine enolate oxidation
• Sharpless epoxidation:




   Example in drug synthesis: Synthesis of Propranolol
• Synthesis of propranolol:


 HO           SiCH3


  SiCH3   H

              OH
      H
• Sharpless epoxidation:




   Example in drug synthesis: Synthesis of Propranolol
O

HO               SiCH3                             HO                SiCH3


                                                                 ArONa
                                                                         ONa


                  CH3
           H3C
         NH
                  NH 2 H                 O
          H3C     CH3

                               OH 4
                               SCH              SiCH3
             OH
     O                     Tetra-n-butylammonium fluoride
                        SCH3                            O   Na
                                       Bu4NF

                                      iprNH2
Synthesis of penicillamin
                                           NaOH or Penicillinase

                                                                                         -     H+
                                                                                         :OH
                                                              R
                                                                      NH             S       CH3
                                                                                              CH3
        H            +                                            O
R       N           OH        ..-                                               N:
                                                                                 -
                                                                            +   NH
            CH2     CH      HS             CH3                                               COOH
                   +                                                   O        OH
                    OH
    O
                                           CH3
                    NH
                    ..-      CH                                                  Decarboxylation
                    H               COOH

                                       R         NH
                                                      C
                                                      CH          S   CH3
                                                      H2

                                            O     O          N        CH3
                                                           OH H
                          Hydrolysis
Synthesis of penicillamin



        H           OH
R       N
            CH2     CH    HS     CH3
                   +
                    OH
    O
                                 CH3
                    NH
                    ..-   CH
                    H          COOH
Synthesis of Aspartame
   MeOOC   H O
                       COOH
           N         NH2
           H     H




                           O
  MeOOC
   HOOC          H
                           C
                 NH            C 3
                               CH
                                           COOH
                                     NH2
                               H
Catalytic asymmetric hydrogenation
               COOH
                       (1)-(R,R)-PNNP-Rh (I) (Cat)
            NHAC                                                  Me
                                                               COOH
                         (1)-H +. MeOH
(z)-2-acetamido-3-phenylacrylic acid                     H   NHAC

                                  S-phenylalanine methyl ester (97 %)
                                  Or (s)- methyl 2-acetamido-3-phenylpropanoate

                       COOMe
                           MeOOC         H
                       NH AC              .. O
                                           +
               H       ..                NH
                                                    COOH
                                         AC
                                              H   NH2
                                             O
                   O                   HO           COOH
             - CH3+C CH3
                  COOH                       H    NH2
              :OH

                                         Aspartic acid
Synthesis of ethambutol          (S,S)


     OH
                H
Me              N
     N                       Me
     H

                HO


                     COOH

                       NH2

          MeS

           L-Methionine
COOH
                  a. MeOH, ACCl
        NH2

MeS          b. ClCOCOCl (0.5 Aq.), Pyridine, CHCl2


                                    COOMe
                                       H                      SMe
                                       N
                                                 H
                                                 N
                           MeS
                                     O
                                             O        COOMe



                                         Oxalyl diamide
COOH                                           COOH
            ..
            NH
                                              ..
              2                               H2N




                                          ..
                                         NH
              COOH
MeS                       .
                         ..                                  MeS




                                               COOH
                          +
                         NH2
      SMe                C     C
                               C
                  Cl -




                                   MeS
                  Cl:               Cl
                                    Cl
                         O
                         O     O
                               O
COOMe                                                COOMe
                                                             COOMeCOOMe
                  COOMe                                             COOMe
                                 Raney Ni, MeOH, H2O
                                                               NH HN HN
                                                                  NH
          NH HN

MeS                                  Desulfuration         Me
                                                           O O         O    O   Me
      O           O        SMe                        MeS
                                                      COOMe    O
                                                Me
                                                                       H             SMe
                                                                       N
                                                       N                            Me
                                                       H
                                                                   O        COOMe


                                                              Penultimate


                                                                 Exhaustive reduction
                                                                 LiAlH4, THF
                             COO H O
                                 Me
                                                 H
                      Me                         N
                                 N                          Me
                                 H
                                            O
                                                     COOH
                                                        Me
                                     Ethambutol
Synthesis of Atenolol
                           O      O       O
                         O N          S
                                          O   O
                 N
      OH         H
           OH
                     S-Glycidylnosylate                 O
                             O                                      O
                                        N
                                  OH H
      CH2CONH2


2-(4-Hydroxyphenyl)acetamide
                                                        CH2CONH2
                               CH2CONH2
                                                    O       O       O
                                                  O N           S
                            Atenolol                                OH
O   O       O
           O N       S
                         O       O
O




CH2CONH2
                             O       O        O CH
                                         S.
                                                  2
                         O N
                                         -.O
                                           ..            O
                                     + H..O +




                                              CH2CONH2
Synthesis of Atenolol
                           O     O       O
                         O N         S                 O
                                         O   O               O
                 N                                                            O
      OH         H                                                                O       O
           OH
                     S-Glycidylnosylate                           +
                                                                            O N       S
                                                                                          OH



      CH2CONH2                                         CH2CONH2
                                                            H3C
2-(4-Hydroxyphenyl)acetamide                                          NH2
                                     Isopropyl amine        H3C




                                                 O          N
                                                       OH   H

                                                                  Atenolol


                                                 CH2CONH2
CH3
           +
          .N
          ..
           .+    CH3
     CH2 H
     .
      .
O     O-

                       O          N
                           OH     H

CH2CONH2

                       CH2CONH2
Anwar.Asymmetric synthesis
Anwar.Asymmetric synthesis
Anwar.Asymmetric synthesis
Anwar.Asymmetric synthesis
Anwar.Asymmetric synthesis

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Anwar.Asymmetric synthesis

  • 1. Asymmetric synthesis Dr. Shaikh A. R
  • 2. • Asymmetric catalytic reduction: Asymmetric catalytic reduction is the use of various chiral catalysts to reduce a pro-chiral organic compound to obtain a chiral product. This is one of the several techniques used in chiral synthesis. e.g. H (g) O O 2 OH O RuCl2 [(R)-BINAP] R OMe MeOH R OMe BINAP=2,2'-bis(diphenylphosphino)-1,1'-binaphthyl The Noyori asymmetric hydrogenation is a chemical reaction described as an asymmetric reduction of β-keto esters. Example in drug synthesis: Synthesis of Naproxen
  • 4. • Asymmetric catalytic oxidation: • Is a technique of oxidising various substrate to give an enantiopure product using a catalyst. • Reactions: • Jacobsen epoxidation of alkenes using manganese- salen complex and NaOCl • Sharpless epoxidation of allyl alcohols using titanium isopropoxide, diethyl tartrate, and t-butyl hydroxyperoxide • Sharpless asymmetric dihydroxylation of alkenes using dihydroquinine or dihydroquinidine ligands on an osmium metal center • Shi epoxidation of alkenes using oxone and a fructose- derived chiral catalyst • Sulfonyloxaziridine enolate oxidation
  • 5. • Sharpless epoxidation: Example in drug synthesis: Synthesis of Propranolol
  • 6. • Synthesis of propranolol: HO SiCH3 SiCH3 H OH H
  • 7. • Sharpless epoxidation: Example in drug synthesis: Synthesis of Propranolol
  • 8. O HO SiCH3 HO SiCH3 ArONa ONa CH3 H3C NH NH 2 H O H3C CH3 OH 4 SCH SiCH3 OH O Tetra-n-butylammonium fluoride SCH3 O Na Bu4NF iprNH2
  • 9. Synthesis of penicillamin NaOH or Penicillinase - H+ :OH R NH S CH3 CH3 H + O R N OH ..- N: - + NH CH2 CH HS CH3 COOH + O OH OH O CH3 NH ..- CH Decarboxylation H COOH R NH C CH S CH3 H2 O O N CH3 OH H Hydrolysis
  • 10. Synthesis of penicillamin H OH R N CH2 CH HS CH3 + OH O CH3 NH ..- CH H COOH
  • 11. Synthesis of Aspartame MeOOC H O COOH N NH2 H H O MeOOC HOOC H C NH C 3 CH COOH NH2 H
  • 12. Catalytic asymmetric hydrogenation COOH (1)-(R,R)-PNNP-Rh (I) (Cat) NHAC Me COOH (1)-H +. MeOH (z)-2-acetamido-3-phenylacrylic acid H NHAC S-phenylalanine methyl ester (97 %) Or (s)- methyl 2-acetamido-3-phenylpropanoate COOMe MeOOC H NH AC .. O + H .. NH COOH AC H NH2 O O HO COOH - CH3+C CH3 COOH H NH2 :OH Aspartic acid
  • 13. Synthesis of ethambutol (S,S) OH H Me N N Me H HO COOH NH2 MeS L-Methionine
  • 14. COOH a. MeOH, ACCl NH2 MeS b. ClCOCOCl (0.5 Aq.), Pyridine, CHCl2 COOMe H SMe N H N MeS O O COOMe Oxalyl diamide
  • 15. COOH COOH .. NH .. 2 H2N .. NH COOH MeS . .. MeS COOH + NH2 SMe C C C Cl - MeS Cl: Cl Cl O O O O
  • 16. COOMe COOMe COOMeCOOMe COOMe COOMe Raney Ni, MeOH, H2O NH HN HN NH NH HN MeS Desulfuration Me O O O O Me O O SMe MeS COOMe O Me H SMe N N Me H O COOMe Penultimate Exhaustive reduction LiAlH4, THF COO H O Me H Me N N Me H O COOH Me Ethambutol
  • 17. Synthesis of Atenolol O O O O N S O O N OH H OH S-Glycidylnosylate O O O N OH H CH2CONH2 2-(4-Hydroxyphenyl)acetamide CH2CONH2 CH2CONH2 O O O O N S Atenolol OH
  • 18. O O O O N S O O O CH2CONH2 O O O CH S. 2 O N -.O .. O + H..O + CH2CONH2
  • 19. Synthesis of Atenolol O O O O N S O O O O N O OH H O O OH S-Glycidylnosylate + O N S OH CH2CONH2 CH2CONH2 H3C 2-(4-Hydroxyphenyl)acetamide NH2 Isopropyl amine H3C O N OH H Atenolol CH2CONH2
  • 20. CH3 + .N .. .+ CH3 CH2 H . . O O- O N OH H CH2CONH2 CH2CONH2