599199-33-4

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 599164-43-9 (4S,5R)-4-methyl-5-phenyl-3-[(E)-phenylprop-2-enoyl]-1,3-oxazolidine-2-thione 

Downstream Products

• 16251-45-9 (4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one 
• 899426-19-8 (4S,5R,2'R,3'R,1''R)-3-[3'-hydroxy-3'-(4-nitrophenyl)-2'-(1''-phenylmethyl)-1''-sulfanylpropionyl]-4-methyl-5-phenyloxazolidin-2-one 

Relevant academic research and scientific papers

Asymmetric induction of three consecutive chiral centers by reactions of N-enoylthioamides with aldehydes

Wrap it up and put on a bow! The reaction of N-cinnamoyl-1,3-oxazoline-2-thione with aromatic aldehydes in the presence of BF3·Et2O diastereoselectively gave adducts 1, which contain three consecutive asymmetric centers and a chiral bridgehead bound to four heteroatoms.

Asymmetric tandem Michael-Aldol reactions between 3-cinnamoyloxazolidine-2- thiones and aldehydes

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.