899426-20-1Relevant articles and documents
Asymmetric tandem Michael-Aldol reactions between 3-cinnamoyloxazolidine-2- thiones and aldehydes
Kinoshita, Hironori,Osamura, Takashi,Mizuno, Kazumi,Kinoshita, Sayaka,Iwamura, Tatsunori,Watanabe, Shin-Ichi,Kataoka, Tadashi,Muraoka, Osamu,Tanabe, Genzoh
, p. 3896 - 3904 (2008/02/06)
Reactions between chiral 3-cinnamoyl-4-methyl-5-phenyl-1,3-oxazolidine-2- thiones and aromatic aldehydes in the presence of BF3·Et 2O diastereoselectively produced tricyclic compounds incorporating a bridgehead carbon bound to four heteroatoms in high yields. Four stereocenters were induced during the reaction. The tricyclic products were transformed into propane-1,3-diols bearing three consecutive stereocenters by acid hydrolysis, S-methylation, and reductive removal of the chiral auxiliary.