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This document describes an enantioselective synthesis of 4H-pyranonaphthoquinones using sequential squaramide and silver catalysis. The reaction involves a one-pot Michael addition/hydroalkoxylation that combines a squaramide-catalyzed Michael addition with a silver-catalyzed hydroalkoxylation. This approach provides the target compounds in moderate to good yields and excellent enantioselectivities using low catalyst loadings. Optimization studies involved screening of different squaramide catalysts and reaction conditions.
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- 1. Enantioselective synthesis of 4H- pyranonaphthoquinones via sequential squaramide and silver catalysis. BY: DATTATRAYA GORE NIPERA1517NP03 MS M.S PHARM(NATURAL PRODUCTS)
- 2. QUICK OVERVIEW 4H-pyranonaphthoquinones were previously synthesized by using bifunctional bis-squaramide catalyst Catalytic screening for asymmetric Micheal addition Optimization studies for hydroalkoxylation reaction One pot Michael addition/ hydroalkoxylation reaction One pot Michael addition/hydroalkoxylation reaction Optimized condition Substrate scope
- 3. Recent approaches for the asymmetric synthesis of pyranonaphthoquinones
- 4. •Squaramide catalyst Michael addition •Metal catalyst hydroalkoxylation Synthetic reaction
- 8. YIELD ENANTIOMERIC EXCESS Squaramide A 91% 84% Squaramide B 92% 85% Squaramide C 99% 82% Squaramide D 98% 83% Squaramide E 92% 88% Squaramide F 94% 68% Squaramide G 97% 79% Squaramide H 96% 73% Squaramide I 97% 71% Squaramide J 91% 88% Squaramide K 94% 96% Squaramide L 98% 81% Squaramide M 93% 85% Squaramide N 96% 80% Squaramide O 94% 90% Squaramide P traces 10%
- 9. HYDROALKOXYLATION Through the π-ACTIVATION of ALKYNE 3a by late TRANSITION METAL COMPLEX 4H-pyranonaphthoquinones (4a)
- 12. 2-hydroxy-1,4-naphthoquinone alkyne-tethered nitroolefin 4H-pyranonaphthoquinones
- 13. Substrate scope for the Michael addition/hydroalkoxylation reaction. 2-hydroxy-1,4-naphthoquinone alkyne-tethered nitroolefin 4H-pyranonaphthoquinones
- 14. Substituents on the nitroalkenes 4 R1 R2 R3 Yield(%) Enantiomeric excess (%) WEAKLY ELECTRON DONATING a H H Ph 93 98 b H H 1-naphthyl 94 96 c H H 2-naphthyl 88 97 ELECTRON WITHDRAWING d H H 2-ClC6H4 81 95 e H H 2-BrC6H4 83 96 f H H 4-CF3C6H4 25 96 ELECTRON RICH g H H 3-MeOC6H4 77 96 h H H 3-MeC6H4 91 96 i H H 2-MeC6H4 93 95 j H H 3,4(-OCH2O-)C6H3 91 92 HETEROARYL k H H 2-furanyl traces - L H H 2-thienyl 23 99 m H H n-butyl 50 95 n H H cyclopenty 19 97
- 15. Substituents on naphthoquinone 4 R1 R2 R3 Yield(%) Enantiomeric excess(%) o MeO H Ph 84 97 p Me Me Ph 86 96 q MeO H 3-MeC6H4 70 97 r MeO H 1-naphthyl 84 97 s Me Me 3,4(-OCH2O)C6H3 76 89 t F H Ph 70 97
- 17. • developed an enantioselective one-pot sequential Michael addition/hydroalkoxylation reaction by combining hydrogen- bonding catalysis and π-activation. • This merger provided substituted 4H-pyranonaphthoquinones in moderate to very good yields and excellent enantioselectivities by using low catalyst loading of squaramide