An efficient asymmetric catalytic hydrogenation of 4-aryl coumarins, preparation of a key intermediate in the synthesis of a class of endothelin receptor antagonists

被引:47
作者
McGuire, MA [1 ]
Shilcrat, SC [1 ]
Sorenson, E [1 ]
机构
[1] SmithKline Beecham Pharmaceut, Dept Synthet Chem, King Of Prussia, PA 19406 USA
关键词
D O I
10.1016/S0040-4039(99)00478-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 4-aryl-3,4-dihydrocoumarin 1 is a critical intermediate in the synthesis of two endothelin receptor antagonists. Asymmetry is introduced by the chiral catalytic hydrogenation of 2. Reduction occurs only if the lactone is open (3). A number of chiral ruthenium and rhodium organometallic species are evaluated as catalysts. The reaction is optimized to produce 1 in high yield and ee. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3293 / 3296
页数:4
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