A new application of Baylis-Hillman alcohols to a diastereoselective synthesis of 3-nitrothietanes

被引：29

作者：

Rai, Ankita ^{[1
]}

Yadav, Lal Dhar S. ^{[1
]}

机构：

[1] Univ Allahabad, Dept Chem, Green Synth Lab, Allahabad 211002, Uttar Pradesh, India

来源：

TETRAHEDRON | 2012年 / 68卷 / 11期

关键词：

Thietanes; Baylis-Hillman adducts; O; O-Diethyl hydrogen phosphorodithioate; Michael addition; Ionic liquids; Stereoselective synthesis; NUCLEOPHILE-INDUCED CYCLIZATION; CONJUGATED NITROALKENES; THIETANE NUCLEOSIDES; SULFOXIDES; MECHANISM; THIIRANES;

D O I：

10.1016/j.tet.2012.01.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three key reactions, the generation of a nucleophile, an thia-Michael addition and an intramolecular cyclisation, were used to achieve an efficient one-pot diastereoseletive synthesis of 3-nitrothietanes. Thus, Baylis-Hillman alcohols and their aldehydes were reacted with either O,O-diethyl hydrogen phosphorodithioate or O,O-diethyl hydrogen phosphorodithioate in combination with a task-specific ionic liquid [bmim]X-Y to afford the corresponding 2,3-di- or 2,3,4-trisubstituted thietanes, respectively. The reaction is high yielding and proceeds with complete diastereoselectivity in favour of the trans isomers. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：2459 / 2464

页数：6

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