Synthesis of functionalized and fused furans and pyrans from the Morita-Baylis-Hillman acetates of nitroalkenes

被引：59

作者：

Nair, Divya K. ^{[1
]}

Mobin, Shaikh M. ^{[1
]}

Namboothiri, Irishi N. N. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 26期

关键词：

Furan; Pyran; Nitroalkene; Morita-Baylis-Hillman acetates; Cascade reaction; POLYSUBSTITUTED FURANS; NITROALLYLIC ACETATES; KETONES;

D O I：

10.1016/j.tetlet.2012.04.084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Morita-Baylis-Hillman (MBH) acetates derived from nitroalkenes and ethyl glyoxylate have been transformed in one pot at room temperature to highly fused and functionalized furans and pyrans in good to excellent yield. The reaction involves a cascade Michael-oxa-Michael addition of beta-dicarbonyl compounds to the MBH acetates in the presence of an amine base such as DABCO. An unusual switching of selectivity in the oxa-Michael addition from 5-exo-trig to 6-endo-trig was observed when the beta-dicarbonyl compound was changed from acyclic or six-membered ring cyclic to five-membered ring cyclic system. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：3349 / 3352

页数：4

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