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 BF3Et2O 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.
Kinoshita
Hironori
H
Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan.
Osamura
Takashi
T
Mizuno
Kazumi
K
Kinoshita
Sayaka
S
Iwamura
Tatsunori
T
Watanabe
Shin-Ichi
S
Kataoka
Tadashi
T
Muraoka
Osamu
O
Tanabe
Genzoh
G
D000447:Aldehydes / Q000737:chemistry*; D001671:Biochemistry / Q000379:methods*; D002934:Cinnamates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013871:Thiones / Q000737:chemistry*
D000447:Aldehydes; D002934:Cinnamates; D013871:Thiones; C116609:3-hydroxybutanal