Stereoselective synthesis of 4-substituted azetidine-2,3-diones by ring opening of 1,3-thiazolidine-derived spiro-β-lactams

被引：11

作者：

Cremonesi, Giuseppe ^{[1
]}

Croce, Piero Dalla ^{[2
,3
]}

Fontana, Francesco ^{[2
,3
]}

La Rosa, Concetta ^{[1
]}

机构：

[1] Ist Chim Organ A Marchesini, Fac Farm, I-20133 Milan, Italy

[2] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

[3] ISTM, CNR, I-20133 Milan, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 05期

关键词：

D O I：

10.1016/j.tetasy.2008.02.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

New 3-heterocycle substituted 1,3-thiazolidine-derived 4-spiro-beta-lactams with a relative trans-configuration were stereoselectively synthesised by means of a Staudinger ketene-imine reaction between the ketene generated from the (2S,4R)-1,3-thiazolidine-2,3,4-tricarboxylic acid 3-(1,1-dimethylethyl) 4-methyl ester 1 and imines 2b-e. The 1,3-thiazolidine-derived 4-spiro-beta-lactams were transformed into the corresponding enantiomerically pure 4-heterocycle substituted azetidine-2,3-diones by means of an oxidative cleavage of the 1,3-thiazolidine ring. The opening of the 1,3-thiazolidine ring was studied under different experimental conditions and a consistent mechanism is proposed. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：554 / 561

页数：8

共 22 条

[21] Synthesis and biological activities of novel 2-(5′-substituted-3′-phenylindole-2′-yl)-1,3,4-oxadiazino[5,6-b]indole and 3-(5′-substituted-3′-phenylindole-2′amido)spiro-(indol-3",2-thiazolidine)-2",4-diones
Biradar, JS
Manjunath, SY
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2004, 43 (02): : 389 - 392
[22] SYNTHETIC APPLICATIONS OF N-N LINKED HETEROCYCLES .16. REACTIONS BETWEEN CARBANIONS DERIVED FROM CARBON ACIDS WITH PKA 7-14 AND N-(2,6-DIMETHYL-4-OXOPYRIDIN-1-YL)PYRIDINIUM TETRAFLUOROBORATE - SYNTHESIS OF 4-SUBSTITUTED PYRIDINES, AND OBSERVATION OF PYRIDINE RING-OPENING REACTIONS
SAMMES, MP
LEUNG, CWF
KATRITZKY, AR
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (11): : 2835 - 2839

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