Trans-Hydroalumination/Alkylation: One-Pot Synthesis of Trisubstituted Allylic Alcohols

Organic Letters 8(17), 3761-3764, DOI: 10.1021/ol0613721

Described herein is a method of stereoselective synthesis of trisubstituted allylic alcohols by alkylation of alkenyl alanates, formed in situ through treatment of propargyl alcohols with Vitride (Red-Al). This technique represents the first of its kind to feature a trans-hydrometalation, and is particularly effective for the formation of 1,4-dienes. Applications involving primary, secondary, and tertiary alcohols are discussed, as well as limitations regarding both alkyne and electrophile components.