Alkylation of alkenes: Ethylaluminum sesquichloride-mediated hydro-alkyl additions with alkyl chloroformates and di-tert-butylpyrocarbonate

U Biermann, JO Metzger

Index: Biermann, Ursula; Metzger, Juergen O. Journal of the American Chemical Society, 2004 , vol. 126, # 33 p. 10319 - 10330

Full Text: HTML

Citation Number: 30

Abstract

A general method for the hydro-alkyl addition to the nonactivated CC double bond of alkenes using alkyl chloroformates (primary, secondary), 12, and di-tert-butylpyrocarbonate, 52, mediated by ethylaluminum sesquichloride (Et3Al2Cl3) has been developed. Reaction of 12 and 52, respectively, with Et3Al2Cl3 gives an alkyl cation which is added to the alkene; hydride transfer to the adduct carbenium ion or, if applicable, 1, 2-H shift followed by ...