DIASTEREODIFFERENTIATING INTRAMOLECULAR CYCLOPROPANATIONS OF PROCHIRAL OLEFINS AND A DIAZO ESTER-LINKED BY OPTICALLY-ACTIVE 2,4-PENTANEDIOL

Authors
MORI A SUGIMURA T TAI A
Citation
A. Mori et al., DIASTEREODIFFERENTIATING INTRAMOLECULAR CYCLOPROPANATIONS OF PROCHIRAL OLEFINS AND A DIAZO ESTER-LINKED BY OPTICALLY-ACTIVE 2,4-PENTANEDIOL, Tetrahedron : asymmetry, 8(5), 1997, pp. 661-664
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
5
Year of publication
1997
Pages
661 - 664
Database
ISI
SICI code
0957-4166(1997)8:5<661:DICOP>2.0.ZU;2-N
Abstract
Intramolecular cyclopropanation of 3, the substrate having a chiral au xiliary as a linking bridge between a diazo ester and cyclohexene, was found to give the cyclopropane 4 having over 99% diastereomeric exces s (d.e.) in 91.5% yield. The reaction was also carried out at 138 degr ees C (p-xylene reflux) to give 4 of 88.2% d.e. (C) 1997 Elsevier Scie nce Ltd.