The Journal of Organic Chemistry

Asymmetric Synthesis of 4-Hydroxy-3-phenyltetrahydroisoquinoline Derivatives Using Enantiopure Sulfinimines (N-Sulfinyl Imines)

FA Davis, YW Andemichael

Index: Davis, Franklin A.; Andemichael, Yemane W. Journal of Organic Chemistry, 1999 , vol. 64, # 23 p. 8627 - 8634

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Citation Number: 37

Abstract

Addition of lateral lithiated amides and phthalide anions to enantiopure sulfinimines (N- sulfinyl imines) represents a new approach for the asymmetric synthesis of 3-substituted isoquinolones and 3-substituted 4-hydroxy isoquinolones, respectively, important chiral building blocks for isoquinoline alkaloid synthesis. In one example 3-phenylisoquinolone (-)- 15b was prepared in> 95% ee by treatment of amide ion 10b with sulfinimine (S)-(+)-11 ...