Improved conditions for the asymmetric synthesis of α-amino acids using Cinchona-derived anthracenylmethyl ammonium salts as chiral phase-transfer organocatalysts

被引：13
作者：
Chinchilla, Rafael
Najera, Carmen
Ortega, Francisco J.
机构：
[1] Univ Alicante, Dept Quim Organ, E-03080 Alicante, Spain
[2] Univ Alicante, Inst Sintesis Organ ISO, E-03080 Alicante, Spain
来源：
TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 24期
关键词：
D O I：
10.1016/j.tetasy.2006.12.004
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Cinchonidine and cinchonine-derived monomeric anthracenylmethyl ammonium salts bearing different counter-anions are used as chiral organocatalysts in the enantioselective alkylation of a benzophenone-imine tert-butyl glycinate under phase-transfer conditions. Generally, an improvement of the enantioselectivity is observed when the counterions are tetrafluoroborate and hexafluorophosphate using 50% aqueous KOH as the base and toluene/chloroform as the solvent. The enantio selectivities achieved are comparable and frequently higher, even working under simpler and less-strict reaction conditions and with lower organocatalyst loading, than those reported previously. (c) 2006 Elsevier Ltd. All rights reserved.
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页码：3423 / 3429
页数：7
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