An efficient asymmetric catalytic hydrogenation of 4-aryl coumarins, preparation of a key intermediate in the synthesis of a class of endothelin receptor antagonists
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作者:
McGuire, MA
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SmithKline Beecham Pharmaceut, Dept Synthet Chem, King Of Prussia, PA 19406 USASmithKline Beecham Pharmaceut, Dept Synthet Chem, King Of Prussia, PA 19406 USA
McGuire, MA
[1
]
Shilcrat, SC
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SmithKline Beecham Pharmaceut, Dept Synthet Chem, King Of Prussia, PA 19406 USASmithKline Beecham Pharmaceut, Dept Synthet Chem, King Of Prussia, PA 19406 USA
Shilcrat, SC
[1
]
Sorenson, E
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SmithKline Beecham Pharmaceut, Dept Synthet Chem, King Of Prussia, PA 19406 USASmithKline Beecham Pharmaceut, Dept Synthet Chem, King Of Prussia, PA 19406 USA
Sorenson, E
[1
]
机构:
[1] SmithKline Beecham Pharmaceut, Dept Synthet Chem, King Of Prussia, PA 19406 USA
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.