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
收藏
页码：576 / 580
页数：5
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