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Organocatalytic Asymmetric Synthesis of 3-Chlorooxindoles Bearing Adjacent Quaternary-Tertiary Centers.
MedLine Citation:
PMID:  22958139     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
A new methodology was developed for the synthesis of enantiomerically enriched 3,3-disubstituted 3-chlorooxindoles 3 via a Michael addition of 3-chloroxindoles to nitroolefins 2, catalyzed by chiral squaramide 10. Products with adjacent quaternary-tertiary centers were isolated in excellent yields (up to 99%), high diastereoselectivities (up to 11:1), and enantiomeric purities (up to 92%). This is the first example where 3-chloroxoindoles 1 have been used as nucleophiles in a highly stereoselective organocatalytic reaction.
Authors:
Artur Noole; Ivar Järving; Franz Werner; Margus Lopp; Andrei Malkov; Tõnis Kanger
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-9-7
Journal Detail:
Title:  Organic letters     Volume:  -     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2012 Sep 
Date Detail:
Created Date:  2012-9-10     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Department of Chemistry, Tallinn University of Technology , Akadeemia tee 15, 12618 Tallinn, Estonia, and Department of Chemistry, Loughborough University , Loughborough LE11 3TU, U.K.
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