Epoxide bond formation and cleavage

1. Epoxide Bond Formation and
Cleavage
Presented By
Gurudutt Dubey
M. Tech. (Pharm.) I Semester
Department of Pharmaceutical Technology (Process Chemistry)
National Institute of Pharmaceutical Education and Research, Mohali, Punjab (India)
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2. Epoxide Bond Formation
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3. KATSUKI-SHARPLESS ASYMMETRIC EPOXIDATION
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J. Am. Chem. Soc. 1980, 102, 5914

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Mechanism:
M= Ti R= i-Pr

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Clayden, J. Warren, S. Greeves, N. Wothers, P. Organic Chemistry, 2001, 1242
Formation of Active Complex

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Clayden, J. Warren, S. Greeves, N. Wothers, P. Organic Chemistry, 2001, 1242
Stereoselectivity:

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J. Am. Chem. Soc. 1962, 84, 867−868
COREY-CHAYKOVSKY REACTION
Mechanism :

8. 8
Preparation of Corey-Chaykovsky Reagent
Dimethyloxosulfonium methylide - known as the Corey Chaykovsky Reagent

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JACOBSEN-KATSUKI EPOXIDATION
J. Am. Chem. Soc. 1991, 113, 7063-7064

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PRILEZHAEV REACTION
Org. Lett. 2003, 5, 3787-3790
Mechanism :

11. Epoxide Bond cleavage
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Clayden, J. Warren, S. Greeves, N. Wothers, P. Organic Chemistry, 2001, 434
Epoxide ring opening by azide

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Ionic liquids/H2O systems for the reaction of epoxides with NaN3 :
a new protocol for the synthesis of 2-azidoalcohols
Tetrahedron Lett. 2005, 46, 6559-6562

14. Regioselective Ring Opening of Epoxides Using NaN3
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Tetrahedron Lett. 2004, 45, 7355–7358

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Polyepoxide-Opening Cascades Promoted by Water
Science. 2007, 317, 1189

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Mechanism:

17. Epoxide Ring Opening Catalyzed by Zinc(II) Perchlorate Hexahydrate
Mechanism:
17
J. Org. Chem. 2007, 72, 10, 3719

18. Synthesis of (RS)/(R)-Propranolols and (RS)/(R)/(S)-Naftopidils
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J. Org. Chem. 2007, 72, 10, 3719

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Asymmetric Catalysis with CO2: Direct Synthesis of Optically Active
Propylene Carbonate from Racemic Epoxides
J. Am. Chem. Soc. 2004, 126, 3733

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Mechanism:

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