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
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
收藏
页码:5160 / 5164
页数:5
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