Asymmetric total synthesis of (+)-exo-brevicomin based on enantioconvergent biocatalytic hydrolysis of an alkene-functionalized 2,3-disubstituted epoxide
In hexane, i.e. under heterogeneous conditions, 1,(omega-1)-dienes readily undergo double deprotonation to give bis(allylmetal) intermediates. In tetrahydrofuran at - 75 or - 50-degrees-C, however, only monometalation occurs with dienes having chains of up to 12 carbon atoms. The practical potential of such selective monosubstitution reactions is demonstrated by two novel pheromone syntheses.
Byrom, Norman T.; Grigg, Ronald; Kongkathip, Boonsong, Journal of the Chemical Society. Perkin transactions I, 1984, # 8, p. 1643 - 1653
作者:Byrom, Norman T.、Grigg, Ronald、Kongkathip, Boonsong、Reimer, Gerald、Wade, Alan R.
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MORET, ETIENNE;DESPONDS, OLIVIER;SCHLOSSER, MANFRED, J. ORGANOMET. CHEM., 409,(1991) N-2, C. 83-91