Enantioselective intramolecular Rauhut-Currier reaction catalyzed by chiral phosphinothiourea

被引：72

作者：

Gong, Jing-Jing ^{[1
,2
]}

Li, Tian-Ze ^{[1
,2
]}

Pan, Kun ^{[1
,2
]}

Wu, Xin-Yan ^{[1
,2
,3
]}

机构：

[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China

[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

[3] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 05期

基金：

中国国家自然科学基金;

关键词：

MORITA-BAYLIS-HILLMAN; AMINO-ACID; PHOSPHINES; CYSTEINE;

D O I：

10.1039/c0cc04412a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral organophosphine-catalyzed enantioselective Rauhut-Currier reaction has been disclosed for the first time. With L-valine-derived phosphinothiourea, the intramolecular Rauhut-Currier reaction of bis(enones) was achieved in good yields (up to 99%) with excellent enantioselectivities (up to 99.4% ee).

引用

页码：1491 / 1493

页数：3

共 19 条

[1] Enantioselective rauhut-currier reactions promoted by protected cysteine [J].

Aroyan, Carrie E. ;

Miller, Scott J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (02) :256-257

[2] Development of a Cysteine-Catalyzed Enantioselective Rauhut-Currier Reaction [J].

Aroyan, Carrie E. ;

Dermenci, Alpay ;

Miller, Scott J. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (17) :5784-5796

[3] The Rauhut-Currier reaction: a history and its synthetic application [J].

Aroyan, Carrie E. ;

Dermenci, Alpay ;

Miller, Scott J. .

TETRAHEDRON, 2009, 65 (21) :4069-4084

[4] Tandem Michael/Michael reactions mediated by phosphines or aryl thiolates [J].

Brown, Paul M. ;

Kappel, Nina ;

Murphy, Patrick J. ;

Coles, Simon J. ;

Hursthouse, Michael B. .

TETRAHEDRON, 2007, 63 (05) :1100-1106

[5] Enantioselective [3+2]-cycloadditions catalyzed by a protected, multifunctional phosphine-containing α-amino acid [J].

Cowen, Bryan J. ;

Miller, Scott J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) :10988-+

[6]

Currier H., 1963, U.S. Patent, Patent No. [307,499,919,630,122, 307499919630122]

[7] A new tandem route to angular tetraquinanes. Synthesis of the waihoensene ring system [J].

ErgUden, JK ;

Moore, HW .

ORGANIC LETTERS, 1999, 1 (03) :375-377

[8] Cooperative, highly enantioselective phosphinothiourea catalysis of imine-allene [3+2] cycloadditions [J].

Fang, Yuan-Qing ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) :5660-+

[9] The vinylogous intramolecular Morita-Baylis-Hillman reaction: Synthesis of functionalized cyclopentenes and cyclohexenes with trialkylphosphines as nucleophilic catalysts [J].

Frank, SA ;

Mergott, DJ ;

Roush, WR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (11) :2404-2405

[10] The enantioselective intramolecular Morita-Baylis-Hillman reaction catalyzed by amino acid-derived phosphinothiourea [J].

Gong, Jing-Jing ;

Yuan, Kui ;

Song, Hong-Liang ;

Wu, Xin-Yan .

TETRAHEDRON, 2010, 66 (13) :2439-2443

← 1 2 →