Diastereoselective ene reactions of triazolinediones with chiral allylic alcohols. Evidence for a hydroxyl-enophile steering effect

被引：9

作者：

Stratakis, M ^{[1
]}

Vassilikogiannakis, G

Orfanopoulos, M

机构：

[1] Univ Cyprus, Dept Nat Sci, Nicosia, Cyprus

[2] Univ Crete, Dept Chem, Iraklion 71409, Greece

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 16期

关键词：

D O I：

10.1016/S0040-4039(98)00207-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ene reaction of PTAD with the chiral allylic alcohol 4-methyl-3-penten-2-ol exhibits high three diastereoselectvity in non polar solvents, whereas in polar solvents the diastereoselectivity decreases substantially. These results are discussed in terms of a steering effect between the hydroxyl and the incoming enophile during: the formation elf the diastereomeric syn and anti aziridinium imide intermediates. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：2393 / 2396

页数：4

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