Vinyl ketones to allenes: preparation of 1,3-dien-2-yl triflates and their application in Pd-catalyzed reactions with soft nucleophiles

Masamichi Ogasawara; Yonghui Ge; Koichi Uetake; Tamotsu Takahashi

doi:10.1021/ol052426u

Vinyl ketones to allenes: preparation of 1,3-dien-2-yl triflates and their application in Pd-catalyzed reactions with soft nucleophiles

Org Lett. 2005 Dec 8;7(25):5697-700. doi: 10.1021/ol052426u.

Authors

Masamichi Ogasawara¹, Yonghui Ge, Koichi Uetake, Tamotsu Takahashi

Affiliation

¹ Catalysis Research Center and Graduate School of Pharmaceutical Sciences, Hokkaido University, and SORST, Japan Science and Technology Agency (JST), Kita-ku, Sapporo 001-0021, Japan. ogasawar@cat.hokudai.ac.jp

PMID: 16321025
DOI: 10.1021/ol052426u

Abstract

[chemical reaction: see text]. A general route of converting alkenyl ketones to functionalized allenes was developed. Substituted 1,3-dien-2-yl triflates, which were prepared from the alkenyl ketones via silyl dienol ethers, were excellent substrates for the palladium-catalyzed reaction with soft nucleophiles giving the multisubstituted allenes in high yields. Comparison between the dienyl triflates and analogous bromodienes in the Pd-catalyzed reaction was studied as well.