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A series of acyclic allylic alcohols of general structure R(1)CH==CHCH(OH)R(2) were resolved by Sharpless kinetic resolution. The hydroxyl groups of these enantiomerically enriched alcohols were derivatized to diethyl phosphates, and the derivatives were reacted with organocopper reagents. Cleanest substitution reactions were observed with reagents… (More)
S(N)2' (gamma) substitutions of delta-substituted allylic acetates with Grignard reagents and copper catalysts proceed with high diastereoselectivities. With benzyloxy, methoxymethoxy, and tert-butyldimethylsiloxy groups, reactions favor the anti-isomer with selectivities up to anti:syn = >99:1. With a hydroxyl group, selectivities are reversed and the… (More)