Enantioselective synthesis of L- and D-carboranylalanine

被引：46
|
作者：
Radel, PA [1 ]
Kahl, SB [1 ]
机构：
[1] UNIV CALIF SAN FRANCISCO,DEPT PHARMACEUT CHEM,SAN FRANCISCO,CA 94143
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 14期
关键词：
D O I：
10.1021/jo952271b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The enantioselective synthesis of L- and D-carboranylalanine is reported. Imides 13 and 14 are treated with titanium tetrachloride, DIEA, and NBS to introduce a bromo functionality in 98:2 ratio at the alpha-center. Azide displacement with TMGA, displacement of the oxazolidinone template with titanium tetrabenzyloxide, and subsequent hydrogenolysis permits L- or D-carboranylalanine to be isolated in high stereoselectivity and 35-40% yields overall.
引用
收藏
页码：4582 / 4588
页数：7
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