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Microwave-Assisted Organocatalytic Enantioselective Intramolecular aza-Michael Reaction with α,β-Unsaturated Ketones.
MedLine Citation:
PMID:  22083999     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
An organocatalytic enantioselective intramolecular aza-Michael reaction of carbamates bearing conjugated ketones as Michael acceptors is described. By using 9-amino-9-deoxy-epi-hydroquinine as the catalyst and pentafluoropropionic acid as a co-catalyst, a series of piperidines, pyrrolidines, and the corresponding benzo-fused derivatives (indolines, isoindolines, tetrahydroquinolines, and tetrahydroisoquinolines) can be obtained in excellent yields and enantioselectivities. In addition, the use of microwave irradiation at 60 °C improves the efficiency of the process giving rise to the final products with comparable yields and enantiomeric excesses. Some mechanistic insights are also considered.
Authors:
Santos Fustero; Carlos Del Pozo; Cristina Mulet; Rubén Lazaro; María Sánchez-Roselló
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-11-14
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  -     ISSN:  1521-3765     ISO Abbreviation:  -     Publication Date:  2011 Nov 
Date Detail:
Created Date:  2011-11-15     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Affiliation:
Departmento de Química Orgánica, Universidad de Valencia, 46100 Burjassot (Spain), Fax: (+34) 963-544-939; Laboratorio de Moléculas Orgánicas, Centro de Investigación Principe Felipe, 46012 Valencia (Spain). santos.fustero@uv.es, sfustero@cipf.es.
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