Development of a tandem base-catalyzed, triphenylphosphine-mediated disulfide reduction-Michael addition

被引：28

作者：

Bartolozzi, Alessandra ^{[1
]}

Foudoulakis, Hope M. ^{[1
]}

Cole, Bridget M. ^{[1
]}

机构：

[1] Surface Logix Inc, Brighton, MA 02135 USA

来源：

SYNTHESIS-STUTTGART | 2008年 / 13期

关键词：

Michael additions; reductions; thiols; triphenylphosphine; benzothiazepinones;

D O I：

10.1055/s-2008-1067102

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tandem disulfide reduction-Michael addition was developed using both free and polymer-bound triphenylphosphine as the reducing agent. The procedure was applied to intermolecular systems for the synthesis of arylsulfanyl- and alkylsulfanyl- sub sti tuted propanoates and related ketones, and to an intramolecular system for the synthesis of a benzothiazepinone derivative.

引用

收藏

页码：2023 / 2032

页数：10

相关论文

共 75 条

[1] Antithrombotic and anticancer effects of garlic-derived sulfur compounds: A review [J].

Ariga, Toyohiko ;

Seki, Taiichiro .

BIOFACTORS, 2006, 26 (02) :93-103

[2]

BAGG MM, 2007, SYNTHESIS-STUTTGART, P457

[3] A new procedure for the preparation of β-keto-δ-lactones from sugars and their transformation into glycosyl accepters in disaccharides synthesis [J].

Bartolozzi, A ;

Capozzi, G ;

Menichetti, S ;

Nativi, C .

ORGANIC LETTERS, 2000, 2 (03) :251-253

[4]

Bartolozzi A, 2001, EUR J ORG CHEM, V2001, P2083, DOI 10.1002/1099-0690(200106)2001:11<2083::AID-EJOC2083>3.0.CO

[5]

2-T

[6] A combinatorial scaffold approach based upon a multicomponent reaction [J].

Bertozzi, F ;

Gundersen, BV ;

Gustafsson, M ;

Olsson, R .

ORGANIC LETTERS, 2003, 5 (09) :1551-1554

[7] FACILE PHOTOCHEMICAL OR OXYGEN INITIATED FREE-RADICAL CHAIN REACTIONS OF TRIALKYLBORANES WITH ORGANIC DISULFIDES - CONVENIENT NEW SYNTHESIS OF ORGANIC SULFIDES VIA HYDROBORATION [J].

BROWN, HC ;

MIDLAND, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (13) :3291-&

[8]

BROWN HC, 1984, SYNTHESIS-STUTTGART, P498

[9] Synthesis and HMG CoA reductase inhibition of 4-thiophenyl quinolines as potential hypocholesterolemic agents [J].

Cai, Zhengyan ;

Zhou, Weicheng ;

Sun, Lixin .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (24) :7809-7829

[10] Diphenyllead(IV) chloride complexes with benzilthiosemicarbazones.: The first bis(thiosemicarbazone) derivatives [J].

Calatayud, David G. ;

Lopez-Torres, Elena ;

Mendiola, M. Antonia .

INORGANIC CHEMISTRY, 2007, 46 (24) :10434-10443

← 1 2 3 4 5 6 7 8 →