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Rhodium-Catalyzed Asymmetric Rearrangement of Alkynyl Alkenyl Carbinols: Synthetic Equivalent to Asymmetric Conjugate Alkynylation of Enones

2007; American Chemical Society; Volume: 129; Issue: 46 Linguagem: Inglês

10.1021/ja076346s

1943-2984

Takahiro Nishimura, Taisuke Katoh, Keishi Takatsu, Ryo Shintani, Tamio Hayashi,

Catalytic C–H Functionalization Methods

Asymmetric 1,3-rearrangement of an alkynyl group of alkynyl alkenyl carbinols giving β-alkynylketones took place in high yields with high enantioselectivity in the presence of a hydroxyrhodium/(R)-binap catalyst. The present method including a key β-alkynyl elimination step in the catalytic cycle is synthetically equivalent to the asymmetric conjugate addition of terminal alkynes to β-substituted enones.