Enantioselective synthesis of 3-functionalized 2-azabicyclo[2.2.1]hept-5-enes by hetero Diels-Alder addition to cyclopentadiene

被引：25

作者：

Blanco, JM

Caamaño, O

Fernández, F

García-Mera, X ^{[1
]}

López, C

Rodríguez, G

Rodríguez-Borges, JE

Rodríguez-Hergueta, A

机构：

[1] Univ Santiago, Fac Farm, Dept Quim Organ, E-15706 Santiago, Spain

[2] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28048 Madrid, Spain

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(98)01102-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diels-Alder cycloaddition of N-benzyl imine of (1R)-8-phenylmenthyl glyoxylate to cyclopentadiene gave the mixture of adducts 3a-d. Major diastereoisomer, the (1S,exo)-adduct (3a), was isolated in 57% yield and transformed in 74% overall yield into (+)-(1S)-N-benzoyl-2-azabicyclo[2.2.1]heptan-3-one (8). which was compared with an authentic sample of its enantiomer. In the course of this transformation sequence, the chiral auxiliary (1R)-8-phenylmenthol was recovered in 90% yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：5663 / 5666

页数：4

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