Stereoselective Lewis Base-Catalyzed Asymmetric Hydrosilylation of α-Acetamido-β-enamino Esters: Straightforward Approach for the Construction of α,β-Diamino Acid Derivatives

被引：24

作者：

Jiang, Yan ^{[1
,2
]}

Chen, Xing ^{[1
,2
]}

Hu, Xiao-Yan ^{[1
,2
]}

Shu, Chang ^{[1
,2
]}

Zhang, Yong-Hong ^{[1
,2
]}

Zheng, Yong-Sheng ^{[1
,2
]}

Lian, Chun-Xia ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

Zhang, Xiao-Mei ^{[1
]}

机构：

[1] Chinese Acad Sci, Key Lab Asymmetr Synth & Chiraltechnol Sichuan Pr, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 10期

关键词：

amino acids; asymmetric catalysis; hydrosilylation; Lewis bases; MANNICH-TYPE REACTION; GLYCINE SCHIFF-BASES; ENANTIOSELECTIVE SYNTHESIS; AMINO-ACIDS; STEREOCONTROLLED SYNTHESIS; ANTITUMOR ANTIBIOTICS; SELECTIVE SYNTHESES; EFFICIENT SYNTHESIS; AROMATIC KETIMINES; IMINES;

D O I：

10.1002/adsc.201300184

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The Lewis base-organocatalyzed asymmetric hydrosilylation of alpha-acetamido-beta-enamino esters was investigated. Among various chiral Lewis base catalysts, a novel catalyst derived from L-serine was found to be the most efficient one which can promote the reaction to afford a series of alpha,beta-diamino acid derivatives with high yields (up to 99%), excellent enantioselectivities (up to 98% ee) and moderate diastereoselectivities (up to 80: 20 dr). The absolute configuration of one of the products was determined by the X-ray crystallographic analysis. In addition, the mechanism and the transition state of the reaction were proposed.

引用

页码：1931 / 1936

页数：6

共 88 条

[21] Trichlorosilane-Mediated Stereoselective Reduction of C=N Bonds [J].

Guizzetti, Stefania ;

Benaglia, Maurizio .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (29) :5529-5541

[22] Highly Stereoselective Metal-Free Catalytic Reduction of Imines: An Easy Entry to Enantiomerically Pure Amines and Natural and Unnatural α-Amino Esters [J].

Guizzetti, Stefania ;

Benaglia, Maurizio ;

Rossi, Sergio .

ORGANIC LETTERS, 2009, 11 (13) :2928-2931

[23] An efficient asymmetric route to 2,3-diaminobutanoic acids [J].

Han, HS ;

Yoon, J ;

Janda, KD .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) :2045-2048

[24]

Hennings DD, 2000, SYNTHESIS-STUTTGART, P1310

[25] Direct Mannich Reaction of Glycinate Schiff Bases with N-(8-Quinolyl)sulfonyl Imines: A Catalytic Asymmetric Approach to anti-α,β-Diamino Esters [J].

Hernandez-Toribio, Jorge ;

Gomez Arrayas, Ramon ;

Carretero, Juan C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (48) :16150-+

[26] Catalytic asymmetric Mannich reaction of glycine Schiff bases with α-amido sulfones as precursors of aliphatic imines [J].

Hernando, Elier ;

Gomez Arrayas, Ramon ;

Carretero, Juan C. .

CHEMICAL COMMUNICATIONS, 2012, 48 (77) :9622-9624

[27] EFFICIENT SYNTHESIS OF α,β-DIAMINO ACID DERIVATIVES BY In(III)-CATALYZED REGIOSELECTIVE ADDITION OF AMINES TO AZIRIDINES [J].

Hu, Xiao-Yu ;

Yang, Xiang-Yu ;

Cheng, Ming ;

Zhang, Qiang ;

Wei, Wei ;

Ji, Jian-Xin .

SYNTHETIC COMMUNICATIONS, 2012, 42 (23) :3403-3412

[28] First chemo- and stereoselective reduction of imines using trichlorosilane activated with N-formylpyrrolidine derivatives [J].

Iwasaki, F ;

Onomura, O ;

Mishima, K ;

Kanematsu, T ;

Maki, T ;

Matsumura, Y .

TETRAHEDRON LETTERS, 2001, 42 (13) :2525-2527

[29] Diastereoselectively Switchable Enantioselective Trapping of Carbamate Ammonium Ylides with Imines [J].

Jiang, Jun ;

Xu, Hua-Dong ;

Xi, Jian-Bei ;

Ren, Bai-Yan ;

Lv, Feng-Ping ;

Guo, Xin ;

Jiang, Li-Qin ;

Zhang, Zhi-Yong ;

Hu, Wen-Hao .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (22) :8428-8431

[30]

Jiang Y., 2011, ANGEW CHEM, V123, P7442

← 1 2 3 4 5 6 7 8 9 →