Solid-phase synthesis of α-alkylserines via phase-transfer catalytic alkylation of polymer-supported 2-phenyl-2-oxazoline-4-carboxylate

被引:2
作者
Lee, Jihye [1 ]
Ha, Min Woo [1 ]
Kim, Taek-Soo [1 ]
Kim, Mi-Jeong [1 ]
Ku, Jin-Mo [1 ]
Jew, Sang-sup [1 ]
Park, Hyeung-geun [1 ]
Jeong, Byeong-Seon [2 ]
机构
[1] Seoul Natl Univ, Pharmaceut Sci Res Inst, Seoul 151742, South Korea
[2] Yeungnam Univ, Coll Pharm, Kyongsan 712749, South Korea
关键词
TERT-BUTYL ESTER; AMINO-ACID-DERIVATIVES; HIGHLY ENANTIOSELECTIVE SYNTHESIS; RESIN-BOUND GLYCINE; ASYMMETRIC-SYNTHESIS; CINCHONA ALKALOIDS; AMMONIUM-SALTS; POLY(ETHYLENE GLYCOL); PEPTIDE-SYNTHESIS; MICHAEL ADDITION;
D O I
10.1016/j.tet.2009.08.052
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Described is the development of a new solid-phase synthetic method for alpha-alkylserines in which phase-transfer catalytic alkylation of polymer-supported 2-phenyl-2-oxazoline-4-carboxylate (12) is the key step. The easy preparation of the polymer-supported substrate 12, the high chemical yield (up to 93%), and the mild cleavage conditions could make this method very practical for the synthesis of a-alkylserines. (c) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8839 / 8843
页数:5
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