%0 Journal Article
%T Stereochemical Studies on the Addition of Allylsilanes to Aldehydes: The S E' Component
%A Denmark
%A Scott E.
%A Almstead
%A Neil G.
%J Journal of the Mexican Chemical Society
%D 2009
%I Sociedad Qu¨ªmica de M¨¦xico
%X model compounds ul -1 and lk-1 have been studied to determine both the position of the silicon electrofuge and the relative orientation of the double bonds in the transition structure of the allylmetal-aldehyde condensation. the use of the deuterium label allows an unbiased assessment of the syn versus anti se' pathways. the synthesis of configurational proof of model systems ul-1 and lk-1 are discussed as well as the cyclization of the model system. cyclization of model 1 was found to proceed with high selectivity via an anti se' pathway regardless of the proximal/distal ratio for all lewis acids studied. reactions promoted by fluoride ion favored the proximal product, but both syn and anti pathways were observed.
%K allyllsilanes
%K addition to aldehides
%K condensation reaction
%K cyclization
%K stereochemistry.
%U http://www.scielo.org.mx/scielo.php?script=sci_abstract&pid=S1870-249X2009000300016&lng=en&nrm=iso&tlng=en