Organocatalytic Asymmetric Synthesis of Pentasubstituted Tetrahydrothiopyrans Bearing a Quaternary Centre through a Double Michael Reaction

被引：5

作者：

Mondal, Buddhadeb ^{[1
]}

Pan, Subhas Chandra ^{[1
]}

机构：

[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India

来源：

SYNLETT | 2018年 / 29卷 / 05期

关键词：

tetrahydrothiopyrans; Michael reaction; organocatalysis; enantioselectivity; quaternary centers; DYNAMIC KINETIC RESOLUTION; PROLINE-DERIVED THIOUREA; CASCADE REACTIONS; DOMINO REACTIONS; TRISUBSTITUTED TETRAHYDROTHIOPHENES; ENANTIOSELECTIVE SYNTHESIS; ADDITION-REACTIONS; FACILE SYNTHESIS; CYCLIC SULFIDES; ALDOL REACTIONS;

D O I：

10.1055/s-0036-1591736

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An organocatalytic, asymmetric, double-Michael strategy has been developed employing trans-cyano-,-unsaturated ketones for the synthesis of pentasubstituted tetrahydrothiopyrans bearing a quaternary center. A proline-derived bifunctional thiourea was found to be the most effective catalyst for this reaction. With 10 mol% of catalyst, good yields and good to high diastereomeric ratios, as well as excellent enantioselectivities, were obtained with a variety of tetrahydrothiopyrans under mild reaction conditions.

引用

页码：576 / 580

页数：5

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