Document Detail


Diastereoselective Additions of Titanium Enolates from N-Glycolyl Thiazolidinethiones to Acetals.
MedLine Citation:
PMID:  22985246     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
The stereochemical outcome of the Lewis acid-mediated glycolate addition of the titanium enolates from protected N-hydroxyacetyl-4-isopropyl-1,3-thiazolidine-2-thiones to dimethyl and dibenzyl acetals depends on the hydroxyl protecting group. Particularly, the pivaloyl protected glycolate derivative provides the reluctant anti adducts in high yields and diastereomeric ratios, which can be isolated and further converted in enantiomerically pure form to β-methoxy or β-benzyloxy α-pivaloyloxy carbonyl fragments in a straightforward manner.
Authors:
Jessica Baiget; Marta Caba; Erik Gálvez; Pedro Romea; Fèlix Urpí; Mercè Font-Bardia
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-9-18
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2012 Sep 
Date Detail:
Created Date:  2012-9-18     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Departament de Química Orgànica, Universitat de Barcelona , Carrer Martí i Franqués 1-11, 08028 Barcelona, Catalonia, Spain.
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