Enantioselective synthesis of 1-alkyl-substituted 1-phenyl-1,2-ethanediols using a myrtenal-derived chiral auxiliary

The enantioselective synthesis of several 1-phenyl-1,2-ethanodiol derivatives using 2-benzoyl-1,3-oxathiane 1 as a chiral auxiliary is described. Nucleophilic additions of Grignard reagents, methyl lithium and LS-Selectride on benzoyloxathiane 1 proceeded in >95% diastereomeric ratio (dr) affordi...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2003-10, Vol.14 (20), p.3225-3232
Main Authors: Vargas-Dı́az, Marı́a Elena, Chacón-Garcı́a, Luis, Velázquez, Pedro, Tamariz, Joaquı́n, Joseph-Nathan, Pedro, Zepeda, L.Gerardo
Format: Article
Language:English
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Summary:The enantioselective synthesis of several 1-phenyl-1,2-ethanodiol derivatives using 2-benzoyl-1,3-oxathiane 1 as a chiral auxiliary is described. Nucleophilic additions of Grignard reagents, methyl lithium and LS-Selectride on benzoyloxathiane 1 proceeded in >95% diastereomeric ratio (dr) affording the corresponding tertiary carbinols, which were successively hydrolyzed and reduced to give the title derivatives in >95% enantiomeric excess (ee). Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2003.07.017