ASYMMETRIC DEPROTONATION AS AN EFFICIENT ENANTIOSELECTIVE PREPARATION OF FUNCTIONALIZED SECONDARY ALCOHOLS

A reaction with organolithium compounds and the chiral amine (-)-sparteine deprotonates carbamates such as 1 in the alpha-position forming chiral lithio compounds 2, as shown by D. Hoppe et al. [Eq. (a)]. These react with high stereoselectivity with a variety of electrophiles to yield nonracemic, chiral compounds (see also the communication on p. 1505 ff). R1 = alkenyl, R2 = C(O)NiPr2, R3 = nBuLi.