New asymmetric approach to β-trifluoromethyl isoserines
Enantiomerically pure N,O-protected beta -trifluoromethyl isoserine derivatives of (2S,3S)- and (2R,3S)-absolute configurations have been easily prepared by diastereoselective addition of the enolates, derived from O-protected alpha -hydroxyacetates, to (S)-N-tert-butanesulfinyl (3,3,3)-trifluoroace...
Saved in:
Published in | RSC advances Vol. 3; no. 18; pp. 6479 - 6484 |
---|---|
Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
01.01.2013
|
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | Enantiomerically pure N,O-protected beta -trifluoromethyl isoserine derivatives of (2S,3S)- and (2R,3S)-absolute configurations have been easily prepared by diastereoselective addition of the enolates, derived from O-protected alpha -hydroxyacetates, to (S)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine with high combined yield and good syn/antistereoselectivity. To explain the unusual stereochemical outcome in these reactions a mechanistic rationale involving the addition of Z-enolates to (S)-imines via open transition states was proposed on the basis of the experimental data. Elaboration of these products via chemoselective manipulation of the protecting groups has been demonstrated. |
---|---|
Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 2046-2069 2046-2069 |
DOI: | 10.1039/c3ra40687c |