Self-reproduction of chirality on α-aminophosphonates:: asymmetric synthesis of α-alkylated diethyl pyrrolidin-2-yl-phosphonate

被引:15
作者
Amedjkouh, M [1 ]
Westerlund, K [1 ]
机构
[1] Univ Gothenburg, Dept Chem, SE-41296 Gothenburg, Sweden
关键词
D O I
10.1016/j.tetlet.2004.04.009
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple method for the asymmetric synthesis of alpha-substituted diethyl pyrrolidin-2-yl-phosphonate is described. The chiral oxazolopyrrolidine phosphonate was alkylated diastereospecifically with an alkyl halide. The key intermediate is an alpha-phosphonate-stabilized carbanion that can be alkylated without loss of optical activity and a single enantiomer of product was formed exclusively in 10-80% yield. The configurational assignment of the products relied on H-1-H-1 NOESY analysis of the alkylated oxazolopyrrolidine phosphonates. This represents an unprecedented case of self-regeneration of stereocenters (SRS) of cyclic aminophosphonates. The enantiomerically pure alpha-aminophosphonate dietlhyl-(2S)-(2-methylpyrrolidin-2-yl)-phosphonate, a surrogate of 2-methyl proline, was obtained upon hydrogenolysis of the chiral auxiliary in 83% yield. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5175 / 5177
页数:3
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