Ligand effects in selective addition reactions of organoindium reagents with carbonyl compounds

Article abstract of DOI:10.1016/S0022-328X(97)00021-1

The reaction of the allyl indium sesquibromide (CH₂ =CHCH₂)₃In₂Br₃ with four equivalents of a bulky lithium alkoxide ((CH₃)₃COLi or (CH₃)₃CCH₂OLi) results in modified reagents which show unusual degrees of chemo-and stereoselectivity in reactions with carbonyl compounds. For example, in reactions with cyclohexanone derivatives, 84-93% equatorial attack with preferential formation of the axial alcohols is observed. Chiral aldehydes react in a highly diastereoselective manner.