Oxazoline formation via a palladium-catalyzed cyclization: A direct, stereoselective approach to cis-5-amino-2-cyclopenten-1-ol derivatives

Alanyl substituted 4-amino-2-cyclopenten-1-yl acetates were obtained optically pure in three steps from cyclopentadiene. The Pd 0 catalyzed cyclization of these allylic acetates was studied using protected and unprotected derivatives. A novel oxazoline synthesis was developed and its utility was dem...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 1995-04, Vol.36 (17), p.2913-2916
Main Authors: Hansel, Jan-Gerd, O'Hogan, Shannon, Lensky, Stephan, Ritter, Allen R., Miller, Marvin J.
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Alanyl substituted 4-amino-2-cyclopenten-1-yl acetates were obtained optically pure in three steps from cyclopentadiene. The Pd 0 catalyzed cyclization of these allylic acetates was studied using protected and unprotected derivatives. A novel oxazoline synthesis was developed and its utility was demonstrated by the preparation of a cis-5-amino-2-cyclopenten-1-ol derivative. Alanyl-substituted cyclopentenyl acetates were readily converted into oxazolines which are useful intermediates in the synthesis of chiral aminocyclopentenols.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(95)00465-O