The first catalytic asymmetric addition of diethylzinc to aldehyde promoted by chiral thiourea

被引：0

作者：

Qiao, Zhi Guo ^{[1
]}

Shen, Tian Hua ^{[1
]}

Fu, Zhen Fang ^{[1
]}

Li, Jun Qi ^{[1
]}

Wang, Hong ^{[1
]}

Song, Qing Bao ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn & Mat Sci, State Key Lab Breeding Base Green Chem Synth Tech, Hangzhou 310032, Zhejiang, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2011年 / 22卷 / 11期

关键词：

Chiral thiourea; Diethylzinc; Amino alcohol; C-2-symmetric; Enantioselective addition; ENANTIOSELECTIVE MICHAEL ADDITION; MANNICH REACTION; ORGANOCATALYSTS; KETONES;

D O I：

10.1016/j.cclet.2011.07.015

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of C-2-symmetric and asymmetric chiral thiourea derivatives were synthesized from commercial L-phenylalanine. All of the new compounds have been fully characterized by IR, H-1 NMR, C-13 NMR, MS spectra and elemental analyses. The chiral thioureas were used as chiral ligands in the catalytic enantioselective ethylation of aldehydes with diethylzinc, the corresponding sec-alcohols were gained with excellent enantioselectivities (up to 87.1% ee) and high yields (up to 76.7%) after the conditions were optimized. (C) 2011 Qing Bao Song. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

引用

页码：1265 / 1268

页数：4

共 20 条

[1] Second-generation organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones [J].

Berkessel, A ;

Mukherjee, S ;

Cleemann, F ;

Müller, TN ;

Lex, J .

CHEMICAL COMMUNICATIONS, 2005, (14) :1898-1900

[2] Novel non-azacyclo 1,2-aminoalcohols derived from L-Phe and highly enantio selective addition of diethylzinc to aryl aldehydes [J].

Da, CS ;

Ni, M ;

Han, ZJ ;

Yang, F ;

Wang, R .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 245 (1-2) :1-7

[3] Discovery of Bifunctional Thiourea/Secondary-Amine Organocatalysts for the Highly Stereoselective Nitro-Mannich Reaction of α-Substituted Nitroacetates [J].

Han, Bo ;

Liu, Qing-Ping ;

Li, Rui ;

Tian, Xu ;

Xiong, Xiao-Feng ;

Deng, Jin-Gen ;

Chen, Ying-Chun .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (27) :8094-8097

[4] Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by a chiral primary amine-thiourea catalyst [J].

Huang, Hongbing ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) :7170-7171

[5] Bifunctional thiourea-promoted cascade aza-Michael-Henry-dehydration reactions: asymmetric preparation of 3-nitro-1,2-dihydroquinolines [J].

Liu, Xiaoqian ;

Lu, Yixin .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (18) :4063-4065

[6] Catalytic asymmetric organozinc additions to carbonyl compounds [J].

Pu, L ;

Yu, HB .

CHEMICAL REVIEWS, 2001, 101 (03) :757-824

[7] A FACILE CONVERSION OF SYMMETRICAL TO UNSYMMETRICAL THIOUREAS [J].

RAMADAS, K ;

SRINIVASAN, N ;

JANARTHANAN, N .

TETRAHEDRON LETTERS, 1993, 34 (40) :6447-6450

[8] A highly enantioselective Bronsted acid catalyst for the Strecker reaction [J].

Rueping, M ;

Sugiono, E ;

Azap, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2617-2619

[9] Schiff base catalysts for the asymmetric Strecker reaction identified and optimized from parallel synthetic libraries [J].

Sigman, MS ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (19) :4901-4902

[10] ENANTIOSELECTIVE ADDITION OF ORGANOZINC REAGENTS TO ALDEHYDES [J].

SOAI, K ;

NIWA, S .

CHEMICAL REVIEWS, 1992, 92 (05) :833-856

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