Open AccessNear absolute regio‐, diastereo‐, and enantioselectivity in a palladium catalyzed alkylation using an uncommon chiral auxiliary
Author(s) -
Sjouken Ronald,
Ebens Rijko,
Kellogg Richard M.
Publication year - 1992
Publication title -
recueil des travaux chimiques des pays‐bas
Language(s) - English
Resource type - Journals
ISSN - 0165-0513
DOI - 10.1002/recl.19921110310
Subject(s) - stereospecificity , alkylation , chemistry , catalysis , palladium , acetal , derivative (finance) , ring (chemistry) , absolute configuration , medicinal chemistry , absolute (philosophy) , tsuji–trost reaction , condensation , diol , stereochemistry , organic chemistry , philosophy , physics , epistemology , financial economics , economics , thermodynamics
Condensation of R‐(+)‐1‐(2‐chlorophenyl)‐2,2‐dimethyl‐propan‐1,3‐diol (2) with a derivative (1) of 1‐formylcyclohexene substituted in the 3‐position with an acetoxy group proceeded with absolute stereospecificity at the acetal center. Catalytic alkylation of the π‐allyl complex obtained upon reaction with Pd with the anion of dimethylamalonate proceeded at the 3‐position of the cyclohexyl ring with complete stereocontrol.