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Enantioselective cyclization/hydrosilylation of 1,6-enynes catalyzed by a cationic rhodium bis(phosphine) complex
Harinath Chakrapani1, Cong Liu, Ross A Widenhoefer
1P. M. Gross Chemical Laboratory, Duke University, Durham, North Carolina 27708-0346, USA.
Organic Letters
|January 17, 2003
Abstract:
[reaction: see text] Reaction of 4,4-dicarbomethoxy-1-octene-6-yne (1) with triethylsilane and a catalytic 1:1 mixture of [Rh(COD)(2)](+) SbF(6)(-) and (R)-BIPHEMP (5 mol %) at 70 degrees C for 90 min gave (Z)-1,1-dicarbomethoxy-3-(1-triethylsilyl)ethylidene-4-methylcyclopentane (2) in 81% isolated yield with 98% de and 92% ee.