Nickel-Catalyzed Highly Enantioselective Hydrogenation of β-Acetylamino Vinylsulfones: Access to Chiral β-Amido Sulfones

被引：63
|
作者：
Long, Jiao [1 ,2 ]
Gao, Wenchao [1 ,2 ]
Guan, Yuqing [1 ,2 ]
Lv, Hui [1 ,2 ,5 ]
Zhang, Xumu [3 ,4 ]
机构：
[1] Wuhan Univ, Key Lab Biomed Polymers, Minist Educ, Wuhan 430072, Hubei, Peoples R China
[2] Wuhan Univ, Coll Chem & Mol Sci, Engn Res Ctr Organosilicon Cpds & Mat, Minist Educ, Wuhan 430072, Hubei, Peoples R China
[3] Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China
[4] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Guangdong, Peoples R China
[5] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 18期
基金：
中国国家自然科学基金;
关键词：
ASYMMETRIC TRANSFER HYDROGENATION; RING-CLOSING METATHESIS; AZA-MICHAEL ADDITION; ALKENE HYDROGENATION; AMINO SULFONES; STEREOSELECTIVE-SYNTHESIS; ALPHA; BETA-UNSATURATED ESTERS; PIPERIDINE-DERIVATIVES; IRON(II) COMPLEXES; KETONES;
D O I：
10.1021/acs.orglett.8b02579
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The nickel/(S)-Binapine complex was found to be an efficient catalyst for asymmetric hydrogenation of beta-acetylamino vinylsulfones to afford chiral beta-Amido sulfones with excellent yields and enantioselectivities (up to 95% yields and >99% ee). This protocol has good compatibility with a series of substituted (Z)-beta-acetylamino vinylsulfones or Z/E isomeric mixtures. A gram-scale reaction has also been achieved in the presence of a 0.2 mol % catalyst loading.
引用
收藏
页码：5914 / 5917
页数：4
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