ENHANCING STEREOSELECTIVITY FROM REACTIONS WITH MODEST GROUP SELECTIVITY

Authors
WARD DE LIU YD RHEE CK
Citation
De. Ward et al., ENHANCING STEREOSELECTIVITY FROM REACTIONS WITH MODEST GROUP SELECTIVITY, Synlett, (8), 1993, pp. 561-563
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
8
Year of publication
1993
Pages
561 - 563
Database
ISI
SICI code
0936-5214(1993):8<561:ESFRWM>2.0.ZU;2-U
Abstract
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- a nd D-gluco-hexanedials with B-isopinocampheyl-9-borabicyclo-[3.3.1]non ane (Alpine-Borane(R)) to give the D-gulacto-, L-galacto-, D-gluco-, a nd L-gulo-hydroxyaldehydes.