Tetrahedron

Asymmetric aza-Diels-Alder reaction: enantio-and diastereoselective reaction of imine mediated by Chiral Lewis acid

K Hattori, H Yamamoto

Index: Hattori, Kouji; Yamamoto, Hisashi Tetrahedron, 1993 , vol. 49, # 9 p. 1749 - 1760

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Citation Number: 175

Abstract

An efficient asymmetric aza-Diels-Alder reaction using chiral boron mediator is developed. The key to its success is the use of the chiral boron complex prepared in situ from (R)-or (S)- binaphthol and B (OPh) 3. The enantiomeric reaction of prochiral imine affords products of up to 90% ee. The double asymmetric induction of chiral imine using α-benzylamine as a chiral auxiliary is achieved with almost complete diastereoselectivity for both aliphatic and ...