Hydroalkylation of alkynyl Ethers via a gold(I)-catalyzed 1,5-hydride shift/cyclization sequence - Archive ouverte HAL Access content directly
Journal Articles Journal of the American Chemical Society Year : 2010

Hydroalkylation of alkynyl Ethers via a gold(I)-catalyzed 1,5-hydride shift/cyclization sequence

(1) , (1) , (1)
1

Abstract

A series of alkynyl ethers react with an electrophilic gold(I) catalyst to produce a range of structurally complex spiro or fused dihydrofurans and dihydropyrans via a 1,5-hydride shift/cyclization sequence. This hydroalkylation process, which is performed under practical experimental conditions, can be applied to terminal as well as ester-substituted alkynes. It allows the efficient conversion of secondary or tertiary sp3 C-H bonds into new C-C bonds by the nucleophilic addition of a vinylgold species onto an oxonium intermediate. The stereoselectivity of the cycloisomerization process toward the formation of a new five- or six-membered cycle appears to be dependent on steric factors and the alkyne substitution pattern. © 2010 American Chemical Society.
Not file

Dates and versions

hal-00951253 , version 1 (28-02-2014)

Identifiers

Cite

Igor D. Jurberg, Yann Odabachian, Fabien Gagosz. Hydroalkylation of alkynyl Ethers via a gold(I)-catalyzed 1,5-hydride shift/cyclization sequence. Journal of the American Chemical Society, 2010, 132 (10), pp.3543-3552. ⟨10.1021/ja9100134⟩. ⟨hal-00951253⟩
112 View
0 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More