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

✍ Scribed by Michael A. McGuire; Susan C. Shilcrat; Edmund Sorenson

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
249 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

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