ALPHA-REGIOSELECTIVE CARBONYL ALLYLATION BY AN ALLYLIC TIN COMPOUND PREPARED FROM 1-BROMOBUT-2-ENE AND TIN(II) BROMIDE AT A NONPOLAR ORGANIC-AQUEOUS INTERFACE
Y. Masuyama et al., ALPHA-REGIOSELECTIVE CARBONYL ALLYLATION BY AN ALLYLIC TIN COMPOUND PREPARED FROM 1-BROMOBUT-2-ENE AND TIN(II) BROMIDE AT A NONPOLAR ORGANIC-AQUEOUS INTERFACE, Journal of the Chemical Society, Chemical Communications, (14), 1995, pp. 1405-1406
1-Bromobut-2-ene on a dichloromethane-water biphasic system at 25 degr
ees C causes alpha-regioselective addition to aldehydes with SnBr2 to
produce 1-substituted pent-3-en-1-ols, and causes gamma-regioselective
addition to aldehydes with SnBr2-Bu(4)NBr to produce 1-substituted 2-
methylbut-3-en-1-ols.