Stereoselective thia-Michael 1,4-Addition to Acyclic 2,4-Dienones and 2-En-4-ynones

被引：17

作者：

Kowalczyk, Rafal ^{[1
]}

Boratynski, Przemyslaw J. ^{[1
]}

机构：

[1] Wroclaw Univ Technol, Dept Organ Chem, PL-50370 Wroclaw, Poland

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 08期

关键词：

conjugate addition; dienones; enynones; organic catalysis; squaramides; thia-Michael addition; CONJUGATE ADDITION; ASYMMETRIC-SYNTHESIS; SULFUR NUCLEOPHILES; COMBINING SILVER; ALIPHATIC THIOLS; ALKYL THIOLS; ORGANOCATALYSIS; AMINES; FUNCTIONALIZATION; SUBSTITUTION;

D O I：

10.1002/adsc.201501138

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Organocatalyzed highly stereoselective 1,4-thia-Michael addition of mercaptans to linear 2,4-dienones and 2-en-4-ynones was developed using Cinchona alkaloid-based squaramides. Application of only 0.5-1mol% loading afforded products in up to 98:2 e.r. and above 99:1 after a single recrystallization. The adducts of allyl mercaptan can be conveniently further transformed to new chiral 2-substituted 2,5-dihydrothiophenes by ring-closing metathesis.

引用

页码：1289 / 1295

页数：7

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