About the stereoselectivity control in reactions of chiral ortho-sulfinyl benzyl carbanions with aldehydes

Reactions of aliphatic and aromatic aldehydes with the benzyllithium derived from 2- p-tolylsulfinyl ethylbenzene yield mixtures of mainly two compounds, anti- 3 and syn- 4 , epimers at hydroxylic carbon, easily separated by chromatography and desulfinylated into enantiomerically pure 1-alkyl (or ar...

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Bibliographic Details
Published in:Tetrahedron 2004-06, Vol.60 (25), p.5383-5392
Main Authors: Garcı́a Ruano, José L, Aranda, M.Teresa, Aguirre, José M
Format: Article
Language:English
Subjects:
1-Alkyl-2-phenyl-1-propanol
1-Aryl-2-phenyl-1-propanol
Benzylic stereocenter
Chiral benzyllithium
Remote stereocontrol
Sulfoxide
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Summary:Reactions of aliphatic and aromatic aldehydes with the benzyllithium derived from 2- p-tolylsulfinyl ethylbenzene yield mixtures of mainly two compounds, anti- 3 and syn- 4 , epimers at hydroxylic carbon, easily separated by chromatography and desulfinylated into enantiomerically pure 1-alkyl (or aryl)-2-phenyl-1-propanols. The observed stereoselectivity at C(1) and C(2) is analyzed to the light of the steric and electronic effects of the substituents. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.04.051