Vinylalumination for the Synthesis of Functionalized Allyl Alcohols, Vinylepoxides, and α-Alkylidene-β-hydroxy-γ-lactones

…, MT Rudd, TE Burghardt, MV Ram Reddy

Index: Ramachandran, P. Veeraraghavan; Rudd, Michael T.; Burghardt, Thomas E.; Ram Reddy, M. Venkat Journal of Organic Chemistry, 2003 , vol. 68, # 24 p. 9310 - 9316

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Citation Number: 43

Abstract

A modified hydroalumination protocol for the preparation of [α-(ethoxycarbonyl) vinyl] diisobutylaluminum and its β-methyl or-phenyl analogues was developed. These vinylaluminum reagents react with aldehydes and ketones to provide the corresponding functionalized allyl alcohols in good to excellent yields. Perfluoroalkyl and-aryl carbonyl compounds, α-keto esters, α-acyl cyanides, and α-acetylenic ketones provide the ...