Enantiopure bicyclic piperidinones: stereocontrolled conjugate additions leading to substituted piperidinones.
The conjugate additions of Reformatsky reagents, organocuprate reagents, and hydroxylamines to a [4.3.0]-bicyclic enelactam derived from 6-oxopipecolic acid have been investigated, and found to be efficient, proceeding with excellent exo-stereocontrol, with the exception of N-benzyl-O-benzylhydroxylamine, which gives predominantly the product of endo-addition. These adducts can be readily converted to substituted piperidinones.
Brewster
Andrew G
AG
The Department of Chemistry, The University of Oxford, Central Research Laboratory, Mansfield Road, Oxford, UK OX1 3TA.
Broady
Simon
S
Hughes
Mark
M
Moloney
Mark G
MG
Woods
Gordon
G