Baylis-Hillman reaction of N-trityl aziridine-2-(S)-carboxaldehyde

被引：41

作者：

Nayak, SK ^{[1
]}

Thijs, L ^{[1
]}

Zwanenburg, B ^{[1
]}

机构：

[1] Univ Nijmegen, Dept Organ Chem, NSR Inst Mol Struct Design & Synth, NL-6525 ED Nijmegen, Netherlands

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 05期

关键词：

D O I：

10.1016/S0040-4039(98)02462-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Trityl aziridine-2-(S)-carboxaldehyde 1 undergoes a facile Baylis-Hillman reaction with a variety of activated vinyl compounds in the presence of a catalytic amount of DABCO to furnish the corresponding adducts 2 in good yields. Unexpectedly, acetylation of the adduct 2a derived from methyl acrylate takes place using Ac2O/py with concomitant allylic transposition. The predominant Z-isomer 4 gives a SN2 type displacement of the acetate with various nucleophiles in contrast to reported SN2' type displacement in similar systems. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：981 / 984

页数：4

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