(2S)-2-[(Phenylsulfinyl)methyl]pyrrolidine-Catalyzed Efficient Stereoselective Michael Addition of Cyclohexanone and Cyclopentanone to Nitroolefins

被引：12

作者：

Singh, Kamal Nain ^{[1
]}

Singh, Paramjit ^{[1
]}

Kaur, Amarjit ^{[1
]}

Singh, Pushpinder ^{[1
]}

Sharma, Sandeep Kumar ^{[1
]}

Khullar, Sadhika ^{[2
]}

Mandal, Sanjay K. ^{[2
]}

机构：

[1] Panjab Univ, Dept Chem, Chandigarh 160014, India

[2] Indian Inst Sci Educ & Res, Dept Chem Sci, Sect 81, Mohali 140306, Punjab, India

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 10期

关键词：

Michael addition reaction; organocatalyst; amino sulfoxide; nitroolefins; ketones; ENANTIOSELECTIVE CONJUGATE ADDITION; CYCLIC-KETONES; NITRO-MICHAEL; BIFUNCTIONAL ORGANOCATALYSTS; METHYL-ETHER; ALDEHYDES; THIOUREA; AMINE; CATALYSTS; ENAMINE;

D O I：

10.1055/s-0032-1316917

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(2S)-2-[(Phenylsulfinyl)methyl]pyrrolidine, derived from L-proline, has been demonstrated as an efficient organocatalyst for the asymmetric Michael addition of cyclohexanone and cyclopentanone to beta-nitrostyrenes. This pyrrolidine-based catalyst bearing a sulfoxide moiety was used to synthesize various gamma-nitro carbonyl compounds in high yield (up to 97%) with excellent stereoselectivity (up to >99:1 dr and >99% ee) without the use of any additive.

引用

页码：1406 / 1413

页数：8

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