Synthesis of Binaphthyl Sulfonimides and Their Application in the Enantioselective Michael Addition of Ketones to Nitroalkenes

被引：39

作者：

Ban, Shurong ^{[1
,2
]}

Du, Da-Ming ^{[1
]}

Liu, Han ^{[3
]}

Yang, Wen ^{[1
]}

机构：

[1] Beijing Inst Technol, Sch Chem Engn & Environm, Beijing 100081, Peoples R China

[2] Shanxi Med Univ, Sch Pharmaceut Sci, Taiyuan 030001, Peoples R China

[3] Peking Univ, BNLMS, Coll Chem & Mol Engn, Beijing 100871, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 27期

基金：

中国国家自然科学基金;

关键词：

Sulfonamides; Organocatalysis; Enantioselectivity; Michael addition; Alkenes; TRANSFER HYDROGENATION ATH; ALDOL REACTIONS; PYRROLIDINE SULFONAMIDE; CONJUGATE ADDITION; DIETHYLZINC ADDITION; ASYMMETRIC ADDITION; TI(IV) COMPLEX; ALDEHYDES; ORGANOCATALYSTS; LIGANDS;

D O I：

10.1002/ejoc.201000818

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel types of L-proline-based binaphthyl sulfonimides and sulfonamides were found to be efficient organocatalysts for the asymmetric Michael addition of ketones to nitroalkenes to provide optically active gamma-nitroketone derivatives of synthetic and biological importance. After the fine optimization of solvents, temperature, and additive, good to excellent enantioselectivities and diastereoselectivities (71-96 % ee, up to >99:1 dr) can be achieved.

引用

页码：5160 / 5164

页数：5

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