140192-46-7Relevant articles and documents
Diastereoselective Alkylation of Carbanions Derived from 1,3-Oxathianes
Perrier, Helene,Huyer, Greg,Young, Robert N.
, p. 725 - 728 (2007/10/02)
Carbanions derived from 4-substituted-1,3-oxathiolane and oxathiane were studied.The magnesium anion of 2-phenyl-4-t-butyldiphenylsilyloxy-1,3-oxathiane reacts with benzaldehyde to give the benzhydrol adduct in a seven to one ratio of diastereoisomers.It was also found that solvent had an effect on site of metalation and in ether 2-phenyl-4-dimethylamino-1,3-oxathiane reacts with s-butyllithium to give ortho metalation.The resulting anion reacts with benzaldehyde to give a 4:1 ratio of diastereoisomers. Key words: chiral carbanion; diastereoselective alkylation; ortho metalation; oxathiane.