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Synlett 1993; 1993(8): 561-563
DOI: 10.1055/s-1993-22528
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Enhancing Stereoselectivity from Reactions with Modest Group Selectivity

Dale E. Ward* , Yadong Liu, Chung K. Rhee
  • *Department of Chemistry, University of Saskatchewan, Saskatoon, Canada S7N 0W0
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Publication Date:
19 March 2002 (online)

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Analysis of the kinetics of certain group selective processes reveals that reactions with only modest group selectivity (3-4:1) can lead to modest yields (50%) of products with high stereoisomeric purity (10-20:1). The analysis is verified by the selective reduction of galacto- and D-gluco-hexanedials with B-isopinocampheyl-9-borabicyclo-[3.3.1]nonane (Alpine-Borane®) to give the D-galacto-, L-galacto-, D-gluco-, and L-gulo-hydroxyaldehydes.