Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/6068
Title: Stereoselective multicomponent assembly of enantiopure oxazolopiperidines and –azepines
Authors: Zill, N
Schoenfelder, A.
Girard, N.
Taddei, Maurizio 
Mann, A.
Issue Date: 2012
Project: None 
Journal: JOURNAL OF ORGANIC CHEMISTRY
Abstract: 
A multicomponent reaction (MCR) based on a cyclohydrocarbonylation (CHC) driven by hydroformylation was set up towards the efficient diastereoselective preparation of oxazolo-piperidines (4a-e) and –azepines (7a-d). The bicyclic oxazolidines were obtained from chiral N-alkenyl amino alcohols via transient cyclic iminium intermediates that underwent an intramolecular cyclization from the appendant oxygen. Based on a series of different experimental conditions, the diastereocontrol observed during the formation of the oxazolidines is best explained by the stereoelectronic effect induced by an 1,3-allylstrain in a common cyclic iminium intermediate (A). This new sequence is suitable for diversity oriented syntheses, allowing the preparation of enantiopure (S)- and (R)-coniceine in five steps from commercially available material
Description: 
54565
URI: http://hdl.handle.net/20.500.12779/6068
ISSN: 0022-3263
Appears in Collections:Publications

Show full item record

Google ScholarTM

Check


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.