Hydrated ?-bonded organometallic cations in organic synthesis. I. Allyl-, crotyl-, 1-methylallyl-, cyclohex-2-enyl-, and cinnamyl-stannation of carbonyl compounds in water

Article abstract of DOI:10.1016/0022-328X(88)89088-0

Homoallylic alcohols can be prepared in water by allyl-, crotyl-, 1-methylallyl-, cyclohex-2-enyl-, or cinnamyl-stannation of such carbonyl compounds as aldehydes, dialdehydes, and ketones, as well as acetals.The procedure is based on: Bu2RSnCl + R'COR" + (1/2)H2O -> R(HO)CR'R" + (1/2)(Bu2SnCl)2O where R = allyl, crotyl, 1-methylallyl, cyclohex-2-enyl, or cinnamyl group, R' = H or alkyl group, R" <*> R'= alkyl group.In most cases, the reaction products are obtained rapidly in high yields (80-100percent).Hydrated organometallic cations Bu2RSn⁺_(aq) are partly involved.These results, together with those already published on 2-propynyl-and allenyl-stannation, indicate the value of this procedure.