Control of enantioselectivity in the photochemical conversion of alpha-oxoamides into beta-lactam derivatives.
[reaction: see text]. Several approaches to asymmetric induction in the alpha-oxoamide (1) to beta-lactam (2) photorearrangement are described. Best results are obtained via irradiation of ionic and covalent chiral auxiliary-containing reactants in the crystalline state and in the interior supercages of zeolites.
Natarajan
Arunkumar
A
Departments of Chemistry, Tulane University, New Orleans, Louisiana 70118, USA.
Wang
Keyan
K
Ramamurthy
V
V
Scheffer
John R
JR
Patrick
Brian
B
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003505:Cyclodextrins; D007651:Keto Acids / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D010072:Oxamic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D010777:Photochemistry; D013237:Stereoisomerism; D017641:Zeolites; D047090:beta-Lactams
D000900:Anti-Bacterial Agents; D003505:Cyclodextrins; D007651:Keto Acids; D047090:beta-Lactams; D017641:Zeolites; D010072:Oxamic Acid