
%0 Journal Article
%A Pyne, SG 
%A Dikic, B 
%A Skelton, BW 
%A White, AH 
%T Chiral Sulfur Compounds. XV. Diastereoselective Additions of Lithiated S-Benzyl-N-t-butyldiphenylsilyl-S-methyl-sulfoximine to Imines and Aldehydes
%J Australian Journal of Chemistry
%D 1992/05/01
%V 45
%N 5
%P 807-822
%K 
%R https://doi.org/10.1071/CH9920807
%U https://www.publish.csiro.au/paper/CH9920807 
%X The lithium salt of racemic S-benzyl-N-t- butyldiphenylsilyl-S-methylsulfoximine (2) undergoes 1,2-addition to imines that have been activated by precomplexation with boron trifluoride diethyl etherate (BF3.Et2O), and aldehydes , with high diastereoselectivity. The relative lS*,2S.*,S*s stereochemistry of the major diastereomeric adducts of (2) and EtCH = NPh and PriCH = NPh , and the relative lS *,2S*,S*s stereochemistry of the major diastereomeric adduct of (2) and propanal were unequivocally determined by single-crystal X-ray structure analysis. An open transition state has been proposed to account for the stereochemical outcome of these reactions. 
