ASYMMETRIC INDUCTION IN THE WITTIG-STILL REARRANGEMENT OF ETHERS CONTAINING AN ALLYLIC STEREOCENTER - DIASTEREOCONTROL BY ALLYLIC NITROGEN

被引：26

作者：

PRIEPKE, H ^{[1
]}

BRUCKNER, R ^{[1
]}

HARMS, K ^{[1
]}

机构：

[1] UNIV MARBURG,FACHBEREICH CHEM,W-3550 MARBURG,GERMANY

来源：

CHEMISCHE BERICHTE | 1990年 / 123卷 / 03期

关键词：

Kew Words: Asymmetric induction / Alcohols, homoallylic, diastereoselective synthesis of / γ‐Amino alcohols, diastereoselective synthesis of / Hydrogen bonding / [2,3] Sigmatropic rearrangement / Wittig rearrangement;

D O I：

10.1002/cber.19901230323

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The stereochemistry of Wittig‐Still rearrangements under the influence of an allylic stereogenic center attached to Bn2N or RNBoc groups is studied. Rearrangements are subject to stereocontrol through asymmetric induction. Stannylated allyl ethers 13 with Z double bonds give syn‐configuration amino alcohols 15 exclusively (ds >95 : < 5 ‐ > 99.8 : < 0.2). Stannanes of E configuration 14 lead to 15 less selectively (syn :anti = 46 : 54 ‐ 92 : 8). X‐ray structural data are provided for amino alcohol syn‐15b and for the bis(carbamate) 17. Copyright © 1990 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

引用

页码：555 / 563

页数：9

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