A general enantioselective synthesis of α‐alkylmalates found in Cephalotaxus and Orchidaceae species is described. This preparation is based upon Seebach’s procedure for the alkylation of D‐malic acid with self‐regeneration of stereogenic centers. Reaction of the dioxolanone 8a with LiHMDS and allyl halides as well as benzyl bromide gave 10 and 14, respectively, which could be transformed into enantiopure α‐alkylmalates 13, 15, 18 and 19. In addition, enantiopure furans of type 20 have been prepared. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
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Bialy et al. (2005) studied this question.
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