Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols

被引：16

作者：

Yang, Hui ^{[1
]}

Zheng, Wen-Hua ^{[1
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, Jiangsu Key Lab Adv Organ Mat, State Key Lab Coordinat Chem, Nanjing 210023, Jiangsu, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 45期

基金：

中国国家自然科学基金;

关键词：

amino alcohols; chiral resolution; kinetic resolution; organotin complexes; MANNICH-TYPE REACTION; BETA-AMINO; ASYMMETRIC AMINOHYDROXYLATION; ACYL TRANSFER; DESYMMETRIZATION; SULFONYLATION; DERIVATIVES; SELECTIVITY; ALLYLATION; TIN;

D O I：

10.1002/anie.201909700

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3 '-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.

引用

页码：16177 / 16180

页数：4

共 59 条

[1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[2]

[Anonymous], ANGEW CHEM

[3]

[Anonymous], 1996, ANGEW CHEM

[4] Stereoselective geminal difunctionalization of vinyl arenes mediated by the bromonium ion [J].

Balaji, Pandur Venkatesan ;

Chandrasekaran, Srinivasan .

CHEMICAL COMMUNICATIONS, 2014, 50 (01) :70-72

[5] The synthesis of vicinal amino alcohols [J].

Bergmeier, SC .

TETRAHEDRON, 2000, 56 (17) :2561-2576

[6] Backbone Modification of β-Hairpin-Forming Tetrapeptides in Asymmetric Acyl Transfer Reactions [J].

Chen, Peng ;

Qu, Jin .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (09) :2994-3004

[7]

Cho I., 2019, ANGEW CHEM, V131, P3170

[8] Enantioselective Aminohydroxylation of Styrenyl Olefins Catalyzed by an Engineered Hemoprotein [J].

Cho, Inha ;

Prier, Christopher K. ;

Jia, Zhi-Jun ;

Zhang, Ruijie K. ;

Gorbe, Tamas ;

Arnold, Frances H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (10) :3138-3142

[9]

Claudio C., 2007, EUR J ORG CHEM, P2561

[10]

Davis A. G., 2008, TIN CHEM FUNDAMENTAL

← 1 2 3 4 5 6 →