Catalytic Enantioselective Addition of Thioacids to Trisubstituted Nitroalkenes

被引：39

作者：

Phelan, James P. ^{[1
]}

Patel, Evan J. ^{[1
]}

Ellman, Jonathan A. ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 42期

关键词：

asymmetric catalysis; michael addition; nitroalkene; organocatalysis; MICHAEL ADDITION; THIOACETIC ACID; DRUG DISCOVERY; DERIVATIVES; OXETANES; MALONATE; ANALOGS;

D O I：

10.1002/anie.201406971

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first example of a catalytic enantioselective addition to and nitronate protonation of trisubstituted nitroalkenes to produce highly enantioenriched products with a tetrasubstituted carbon is reported. Thioacids added in excellent yields and with high enantioselectivities to both activated and unactivated nitroalkenes. The 1,2-nitrothioacetate products can be readily converted in two steps to biomedically relevant 1,2-aminosulfonic acids without loss of enantiopurity.

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收藏

页码：11329 / 11332

页数：4

相关论文

共 38 条

[1] A general one-step synthesis of β-nitronitriles [J].

Anderson, James C. ;

Blake, Alexander J. ;

Mills, Matthew ;

Ratcliffe, Paul D. .

ORGANIC LETTERS, 2008, 10 (18) :4141-4143

[2]

Berner OM, 2002, EUR J ORG CHEM, V2002, P1877

[3] Synthesis and Stability of Oxetane Analogs of Thalidomide and Lenalidomide [J].

Burkhard, Johannes A. ;

Wuitschik, Georg ;

Plancher, Jean-Marc ;

Rogers-Evans, Mark ;

Carreira, Erick M. .

ORGANIC LETTERS, 2013, 15 (17) :4312-4315

[4] Cascade Formation of Isoxazoles: Facile Base-Mediated Rearrangement of Substituted Oxetanes [J].

Burkhard, Johannes A. ;

Tchitchanov, Boris H. ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (23) :5379-5382

[5] Oxetanes as Versatile Elements in Drug Discovery and Synthesis [J].

Burkhard, Johannes A. ;

Wuitschik, Georg ;

Rogers-Evans, Mark ;

Mueller, Klaus ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (48) :9052-9067

[6] Facile synthesis of various substituted taurines, especially syn- and anti-1,2-disubstituted taurines, from nitroolefins [J].

Chen, Ning ;

Xu, Jiaxi .

TETRAHEDRON, 2012, 68 (11) :2513-2522

[7] CONVERSION OF NITROALKENES INTO BETA-(TRICHLOROMETHYL)NITROALKANES [J].

CUNICO, RF ;

ZHANG, CP .

SYNTHETIC COMMUNICATIONS, 1991, 21 (21) :2189-2195

[8] The use of taurine analogues to investigate taurine functions and their potential therapeutic applications [J].

Della Corte, L ;

Crichton, RR ;

Duburs, G ;

Nolan, K ;

Tipton, KF ;

Tirzitis, G ;

Ward, RJ .

AMINO ACIDS, 2002, 23 (04) :367-379

[9] Asymmetric organocatalysis: From infancy to adolescence [J].

Dondoni, Alessandro ;

Massi, Alessandro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) :4638-4660

[10] Small-molecule H-bond donors in asymmetric catalysis [J].

Doyle, Abigail G. ;

Jacobsen, Eric N. .

CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743

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