ROTATIONAL FEATURES OF CARBON-NITROGEN BONDS IN AXIALLY CHIRAL O-TERT-BUTYL ANILIDES AND RELATED MOLECULES - POTENTIAL SUBSTRATES FOR THE PROCHIRAL AUXILIARY APPROACH TO ASYMMETRIC-SYNTHESIS

Authors
CURRAN DP HALE GR GEIB SJ BALOG A CASS QB DEGANI ALG HERNANDES MZ FREITAS LCG
Citation
Dp. Curran et al., ROTATIONAL FEATURES OF CARBON-NITROGEN BONDS IN AXIALLY CHIRAL O-TERT-BUTYL ANILIDES AND RELATED MOLECULES - POTENTIAL SUBSTRATES FOR THE PROCHIRAL AUXILIARY APPROACH TO ASYMMETRIC-SYNTHESIS, Tetrahedron : asymmetry, 8(23), 1997, pp. 3955-3975
Citations number
43
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
23
Year of publication
1997
Pages
3955 - 3975
Database
ISI
SICI code
0957-4166(1997)8:23<3955:RFOCBI>2.0.ZU;2-#
Abstract
A new strategy for asymmetric induction termed the 'prochiral auxiliar y' approach is introduced. Reactions of acylating agents with prochira l N-methyl-o-tert-butyl aniline provide anilides that are axially chir al by virtue of restricted rotation about the N-Ar bond, Rotamer popul ations about the amide bond (E/Z) were studied by H-1 NMR. Several pai rs of enantiomeric o-tert-butyl anilides were separated by chiral chro matography and barriers about the N-Ar bond were measured by thermal r acemization. Related o-(1-(trialkylsilyloxy)-1-methylethyl) anilides w ere also studied. (C) 1997 Published by Elsevier Science Ltd. All righ ts reserved.