Diastereoselective cycloadditions of 1,3-thiazolium-4-olates with chiral 1,2-diaza-1,3-butadienes

被引：31

作者：

Avalos, M ^{[1
]}

Babiano, R

Cintas, P

Clemente, FR

Gordillo, R

Jiménez, JL

Palacios, JC

Raithby, PR

机构：

[1] Univ Extremadura, Fac Ciencias, Dept Quim Organ, E-06071 Badajoz, Spain

[2] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 17期

关键词：

D O I：

10.1021/jo991841v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 2-(N-methyl)benzylamino-1,3-thiazolium-4-olates (2-aminothioisomunchnones) react with chiral 1,2-diaza-1,3-butadienes derived from carbohydrates to afford a diastereomeric mixture of (4R,5S)- and (4R,5R)-4,5-dihydrothiophenes. These substrate-controlled cycloadditions are chemoselective, regiospecific, and proceed with a high facial diastereoselection. A theoretical rationale at semiempirical level does justify the stereochemical outcome observed in the experiments.

引用

页码：5089 / 5097

页数：9

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