Enantioselective synthesis of m-carboranylalanine, a boron-rich analogue of phenylalanine

被引：20
|
作者：
Naeslund, C [1 ]
Ghirmai, S [1 ]
Sjöberg, S [1 ]
机构：
[1] Uppsala Univ, Dept Chem, BMC, SE-75124 Uppsala, Sweden
来源：
TETRAHEDRON | 2005年 / 61卷 / 05期
关键词：
m-carboranylalanine; absolute configuration; carborane; Boron neutron capture therapy; asymmetric synthesis; highly lipophilic amino acid;
D O I：
10.1016/j.tet.2004.11.045
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The enantiomers of the highly lipophilic alpha-amino acid m-carboranyl-alanine [3-(1,7-dicarba-closo-dodecaborane(12)-1-yl)-2-aminopropanoic acid], a carborane containing analogue of phenylalanine, have been synthesised via hydroxyamination of the N-acyl derivative formed from 3-(m-carboranyl)propionic acid [3-(1,7-dicarba-closo-dodeca-borane(12)-1-yl)-2-propanoic acid] and Oppolzer's camphor sultam. The enantiomeric excess of both enantiomers of the amino acid was >98%. (S)-Configuration was assigned to the (+)-enantiomer (CH3OH, 589 nm). (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1181 / 1186
页数：6
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