Kinetic resolution of racemic lactones by conjugate additions of allylic organolithium species: direct formation of three contiguous centers with high diastereo- and enantioselectivities |
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| Authors: | Lim Sung H Beak Peter |
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| Institution: | Department of Chemistry, University of Illinois at Urbana-Champaign, 61801, USA. |
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| 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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