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An Enantioselective Approach towards 3,4-Dihydroisocoumarin through the Bromocyclization of Styrene-type Carboxylic Acids.
MedLine Citation:
PMID:  22175914     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
A facile and enantioselective approach towards 3,4-dihydroisocoumarin was developed. The method involved an amino-thiocarbamate catalyzed enantioselective bromocyclization of styrene-type carboxylic acids, yielding 3-bromo-3,4-dihydroisocoumarins with good yields and ees. 3-bromo-3,4-dihydroisocoumarins are versatile building blocks for various dihydroisocoumarin derivatives in which the Br group can readily be modified to achieve biologically important 4-O-type and 4-N-type 3,4-dihydroisocoumarin systems. In addition, studies indicated that by refining some parameters, the synthetically useful 5-exo phthalide products could be achieved with good yields and ees.
Authors:
Jie Chen; Ling Zhou; Chong Kiat Tan; Ying-Yeung Yeung
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-12-16
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  -     Publication Date:  2011 Dec 
Date Detail:
Created Date:  2011-12-19     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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