Enantioselective cyclization/hydrosilylation of 1,6-enynes catalyzed by a cationic rhodium bis(phosphine) complex.
[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.
Chakrapani
Harinath
H
P. M. Gross Chemical Laboratory, Duke University, Durham, North Carolina 27708-0346, USA.
Liu
Cong
C
Widenhoefer
Ross A
RA
D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis; D009942:Organometallic Compounds / Q000737:chemistry; D012235:Rhodamines / Q000737:chemistry*; D013237:Stereoisomerism
D000466:Alkadienes; D006844:Hydrocarbons, Cyclic; D009942:Organometallic Compounds; D012235:Rhodamines