共 57 条
Synthesis of Binaphthyl Sulfonimides and Their Application in the Enantioselective Michael Addition of Ketones to Nitroalkenes
被引:39
作者:

Ban, Shurong
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机构:
Beijing Inst Technol, Sch Chem Engn & Environm, Beijing 100081, Peoples R China
Shanxi Med Univ, Sch Pharmaceut Sci, Taiyuan 030001, Peoples R China Beijing Inst Technol, Sch Chem Engn & Environm, Beijing 100081, Peoples R China

Du, Da-Ming
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Beijing Inst Technol, Sch Chem Engn & Environm, Beijing 100081, Peoples R China Beijing Inst Technol, Sch Chem Engn & Environm, Beijing 100081, Peoples R China

Liu, Han
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机构:
Peking Univ, BNLMS, Coll Chem & Mol Engn, Beijing 100871, Peoples R China Beijing Inst Technol, Sch Chem Engn & Environm, Beijing 100081, Peoples R China

Yang, Wen
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机构:
Beijing Inst Technol, Sch Chem Engn & Environm, Beijing 100081, Peoples R China Beijing Inst Technol, Sch Chem Engn & Environm, Beijing 100081, Peoples R China
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.
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页码:5160 / 5164
页数:5
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