A highly stereoselective synthesis of chiral alpha-amino-beta-lactams via the Kinugasa reaction employing ynamides.
A highly stereoselective synthesis of chiral alpha-amino-beta-lactam through an ynamide-Kinugasa reaction is described. In addition, a mechanistic model is illustrated here to rationalize the observed diastereoselectivity, which depends on both the initial [3 + 2] cycloaddition step and the subsequent protonation for which both are highly selective.
Zhang
Xuejun
X
Division of Pharmaceutical Sciences and Department of Chemistry, 777 Highland Avenue, University of Wisconsin, Madison, Wisconsin 53705-2222, USA.
Hsung
Richard P
RP
Li
Hongyan
H
Zhang
Yu
Y
Johnson
Whitney L
WL
Figueroa
Ruth
R
D000480:Alkynes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D000577:Amides; D047090:beta-Lactams