Kinetic resolution of amines: A highly enantioselective and chemoselective acetylating agent with a unique solvent-induced reversal of stereoselectivity

被引：94

作者：

Arseniyadis, S

Valleix, A

Wagner, A

Mioskowski, C

机构：

[1] Fac Pharm, CNR, Lab Synth Bioorgan, UMR 7514, F-67400 Illkirch Graffenstaden, France

[2] CEA Saclay, Serv Mol Marquees, F-91191 Gif Sur Yvette, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 25期

关键词：

acylation; enantioselectivity; kinetic resolution; solvent effects;

D O I：

10.1002/anie.200453956

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Solvents lend a hand: Changing the polarity of the reaction solvent from 1,3-dimethyltetrahydropyrimidin-2-one (DMPU) to toluene reverses the stereo-selectivity observed in the acetylation of amines with (1S,2S)-1 (see scheme). Optimizing the reaction conditions led to an unprecedented 90% ee (S) in DMPU at -20°C with a 33% conversion.

引用

页码：3314 / 3317

页数：4

共 4 条

[1] Escherichia coli BioH: a highly enantioselective and organic solvent tolerant esterase for kinetic resolution of sec-alcohols
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Tang, Xiaoling
Liu, Ji
Yu, Hongwei
TETRAHEDRON LETTERS, 2010, 51 (48) : 6360 - 6364
[2] N-Octanoyldimethylglycine Trifluoroethyl Ester, an Acyl Donor Leading to Highly Enantioselective Protease-Catalysed Kinetic Resolution of Amines
Queyroy, Severine
Vanthuyne, Nicolas
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ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (09) : 1759 - 1764
[3] Side-Arm-Promoted Highly Enantioselective Ring-Opening Reactions and Kinetic Resolution of Donor-Acceptor Cyclopropanes with Amines
Zhou, You-Yun
Wang, Li-Jia
Li, Jun
Sun, Xiu-Li
Tang, Yong
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (22) : 9066 - 9069
[4] Highly enantioselective kinetic resolution of primary alcohols of the type Ph-X-CH(CH3)-CH2OH by Pseudomonas cepacia lipase:: effect of acyl chain length and solvent
Mezzetti, A
Keith, C
Kazlauskas, RJ
TETRAHEDRON-ASYMMETRY, 2003, 14 (24) : 3917 - 3924

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