SYNTHESIS OF (S)-2-AMINO-1,1-DIPHENYLBUTAN-4-OL - CONVERSION OF AN ALPHA-AMINO-ACID INTO AN ALPHA-(DIPHENYLMETHYL) AMINE WITHOUT LOSS OF OPTICAL PURITY

被引:32
作者
BOYLE, PH [1 ]
DAVIS, AP [1 ]
DEMPSEY, KJ [1 ]
HOSKEN, GD [1 ]
机构
[1] TRINITY COLL DUBLIN,DEPT CHEM,DUBLIN 2,IRELAND
关键词
D O I
10.1016/0957-4166(95)00373-W
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The title amino-alcohol 4 is an intermediate for the preparation of chiral bicyclic amidines and guanidines, and also for polyamines with potential as ligands in enantioselective catalysis. It has been synthesized from (S)-methionine 1 via (S)-homoserine lactone 2 and amino-diol 3. Hydrogenolysis of the doubly benzylic hydroxyl group in 3 proved non-trivial, but was eventually achieved through the application of catalytic transfer methodology to the bis-acetyl derivative 14.
引用
收藏
页码:2819 / 2828
页数:10
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