Journal
TETRAHEDRON
Volume 58, Issue 37, Pages 7545-7552Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(02)00577-X
Keywords
asymmetric epoxidation; ulose; D-glucose
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Three ulose catalysts (1-3) were prepared from D-glucose via an intramolecular nitrile oxide cycloaddition (INOC) as the key step. The enantioselectivity of ulose 2 and 3 in asymmetric epoxidation was poor (up to 26% ee). Ulose 1 afforded good chemical yields (up to 83% yield) and the enantiomeric excess is up to 71% for the formation of (-)-trans-stilbene oxide. (C) 2002 Elsevier Science Ltd. All rights reserved.
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