Synthesis of chiral nonracemic homo-1-deoxyazasugars with D-talo-and L-allo-configuration via tandem Wittig [2+3] cycloaddition reaction

被引：43

作者：

Herdeis, C

Schiffer, T

机构：

[1] Inst. F. Pharm. L., D-97074 Würzburg, Am Hubland

来源：

TETRAHEDRON | 1996年 / 52卷 / 47期

关键词：

D O I：

10.1016/0040-4020(96)00949-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Wittig reaction of 6a,b proceeds with concomitant 1,3-dipolar cycloaddition of the azido function to the nonisolable triazoline 20 which isomerizes to diazoamine 7. Elimination of nitrogen from 7 provides vinylogous urethane 8 which can be transformed to heterocyclic beta-amino acid 10 and D-homo-1-deoxyazatalose (13). Catalytic hydrogenation of 7 and manipulation of functional groups give L-homo-1-deoxyazaallose (16) and beta-amino acid 18. Copyright (C) 1996 Elsevier Science Ltd

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页码：14745 / 14756

页数：12

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