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

被引：60

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

页码：5914 / 5917

页数：4

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