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

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

*Department of Chemistry, Graduate School of Science, Kyoto University, Kyoto 606-8502, Japan, Email: tnishikuchem.kyoto-u.ac.jp, thayashikuchem.kyoto-u.ac.jp

T. Nishimura, T. Katoh, K. Takatshu, R. Shintani, T. Hayashi, J. Am. Chem. Soc., 2007, 129, 14158-14159.

DOI: 10.1021/ja076346s (free Supporting Information)


Abstract

An asymmetric 1,3-rearrangement of an alkynyl group of alkynyl alkenyl carbinols took place in the presence of a hydroxyrhodium/(R)-binap catalyst to yield β-alkynylketones in high yields with high enantioselectivity. The present method includes a key β-alkynyl elimination step in the catalytic cycle.

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Key Words

Alkynylation, Conjugate Addition


ID: J48-Y2007-3610