HOMOCHIRAL 2,2'-BIS(OXAZOLYL)-1,1'-BINAPHTHYLS AS LIGANDS FOR COPPER(I)-CATALYZED ASYMMETRIC CYCLOPROPANATION

Authors
UOZUMI Y KYOTA H KISHI E KITAYAMA K HAYASHI T
Citation
Y. Uozumi et al., HOMOCHIRAL 2,2'-BIS(OXAZOLYL)-1,1'-BINAPHTHYLS AS LIGANDS FOR COPPER(I)-CATALYZED ASYMMETRIC CYCLOPROPANATION, Tetrahedron : asymmetry, 7(6), 1996, pp. 1603-1606
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
6
Year of publication
1996
Pages
1603 - 1606
Database
ISI
SICI code
0957-4166(1996)7:6<1603:H2ALFC>2.0.ZU;2-E
Abstract
Homochiral 2,2'-bis[4-(alkyl)oxazol-2-yl]-1,1'-binaphthyls, which poss ess both binaphthyl axial chirality and carbon centred chirality, were prepared from 1,1'-binaphthyl-2,2'-dicarboxylic acid and 2-alkyl-2-am inoethanols in high yields. Asymmetric cyclopropanation of styrene wit h diazoacetates in the presence of 2 mol % of copper(I) triflate and 2 '-bis[(S)-4-(t-butyl)oxazol-2-yl]-1,1'-binaphthyl gave optically activ e 2-(phenyl)cyclopropane-carboxylates of up to 97% ee. (C) 1996 Elsevi er Science Ltd