Thieme Chemistry Journal Awardees - Where Are They Now? Bifunctional Silver Acetate Catalyzed Asymmetric Mannich-Type Reactions

被引：32

作者：

Chen, Qing-An ^{[1
]}

Zeng, Wei ^{[1
]}

Wang, Da-Wei ^{[1
]}

Zhou, Yong-Gui ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

来源：

SYNLETT | 2009年 / 14期

关键词：

bifunctional; silver acetate; Mannich reaction; asymmetric catalysis; imines; CHIRAL BRONSTED ACID; ALPHA-AMIDO SULFONES; HIGHLY ENANTIOSELECTIVE SYNTHESIS; VINYLOGOUS MANNICH; BETA-AMINO; N-BOC; ANTI-MANNICH; 3-PYRROLIDINECARBOXYLIC ACID; GLYCINE DERIVATIVES; CINCHONA ALKALOIDS;

D O I：

10.1055/s-0029-1217805

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient bifunctional silver acetate catalyzed three asymmetric Mannich-type reactions with high reactivity, Lip to >95:5 diastereoselectivities and moderate to excellent enantioselectivities (Lip to 97% ee). External base is not required in this bifunctional catalytic procedure, in which acetate promotes the deprotonation.

引用

页码：2236 / 2241

页数：6

共 118 条

[1] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].

Akiyama, T ;

Itoh, J ;

Yokota, K ;

Fuchibe, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568

[2] Vinylogous Mannich-type reaction catalyzed by an iodine-substituted chiral phosphoric acid [J].

Akiyama, Takahiko ;

Honma, Yasuhiro ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) :399-402

[3]

Arend M, 1999, ANGEW CHEM INT EDIT, V38, P2873, DOI 10.1002/(SICI)1521-3773(19991004)38:19<2873::AID-ANIE2873>3.0.CO

[4]

2-P

[5] Catalytic asymmetric Mannich reactions of glycine derivatives with imines.: A new approach to optically active α,β-diamino acid derivatives [J].

Bernardi, L ;

Gothelf, AS ;

Hazell, RG ;

Jorgensen, KA .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2583-2591

[6] A highly efficient and practical method for catalytic asymmetric vinylogous Mannich (AVM) reactions [J].

Carswell, Emma L. ;

Snapper, Marc L. ;

Hoveyda, Amir H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (43) :7230-7233

[7] The Proline-Catalyzed Double Mannich Reaction of Acetaldehyde with N-Boc Imines [J].

Chandler, Carley ;

Galzerano, Patrizia ;

Michrowska, Anna ;

List, Benjamin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (11) :1978-1980

[8] A bench-stable homodinuclear Ni2-chiff base complex for catalytic asymmetric synthesis of α-tetrasubstituted anti-α,β-diamino acid surrogates [J].

Chen, Zhihua ;

Morimoto, Hiroyuki ;

Matsunaga, Shigeki ;

Shibasaki, Masakatsu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (07) :2170-+

[9] The direct catalytic asymmetric Mannich reaction [J].

Córdova, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (02) :102-112

[10] A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives [J].

Córdova, A ;

Watanabe, S ;

Tanaka, F ;

Notz, W ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1866-1867

← 1 2 3 4 5 6 7 8 9 10 →