Kinetic resolution of 2-hydroxy-2-aryl-ethylphosphonates by a non-enzymatic acylation catalyst

被引：7
|
作者：
Mesas-Sanchez, Laura [1 ]
Diaz-Alvarez, Alba E. [1 ]
Koukal, Peter [1 ]
Diner, Peter [1 ,2 ]
机构：
[1] Uppsala Univ, Dept Chem, BMC, SE-75123 Uppsala, Sweden
[2] KTH Royal Inst Technol, Dept Chem, SE-10044 Stockholm, Sweden
来源：
TETRAHEDRON | 2014年 / 70卷 / 24期
关键词：
Non-enzymatic kinetic resolution; 2-Hydroxy-2-arylethylphosphonates; Planar chiral DMAP derivative catalyst; B RECEPTOR ANTAGONISTS; ASYMMETRIC-SYNTHESIS; SECONDARY ALCOHOLS; ENANTIOSELECTIVE HYDROGENATION; SEX-PHEROMONE; ACYL-TRANSFER; GABA; PHOSPHONATES; DMAP; ACID;
D O I：
10.1016/j.tet.2014.03.102
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Optically pure hydroxyphosphonates are widely used as derivatizable compounds that can be incorporated into a variety of synthetic strategies for the preparation of other high value organic products. A non-enzymatic kinetic resolution procedure to obtain chiral 2-hydroxy-2-arylethylphosphonates from the easily available racemic counterparts is described. A range of 2-hydroxy-2-arylethylphosphonates was efficiently resolved employing a planar-chiral DMAP derived catalyst with good selectivities (up to S=68). The chiral hydroxyphosphonates were isolated in good yields and high enantiomeric excess (>94% ee). (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3807 / 3811
页数：5
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