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  • Title: Kinetic resolution of racemic lactones by conjugate additions of allylic organolithium species: direct formation of three contiguous centers with high diastereo- and enantioselectivities.
    Author: Lim SH, Beak P.
    Journal: Org Lett; 2002 Aug 08; 4(16):2657-60. PubMed ID: 12153202.
    Abstract:
    [reaction: see text] Kinetic resolution of racemic alpha,beta-unsaturated lactones by the organolithium species produced from asymmetric lithiation of N-Boc-N-(p-methoxyphenyl)cinnamylamine provides conjugate addition products with three contiguous stereogenic centers in yields of 62-77% with diastereomeric ratios from 75:25 to >99:1 and enantiomeric ratios for the major diastereomers from 94:6 to 98:2.
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