PREPARATION OF BETA-LACTAMS BY THE CONDENSATION OF LITHIUM ESTER ENOLATES WITH ARYL ALDIMINES Academic Article uri icon

abstract

  • The condensation of simple lithium ester enolates with appropriately substituted aryl imines produces -lactams in yields from 35 to 95%. Excellent stereoselectivity is observed in the preparation of -lactams with chiral centers at C-3 and C-4 of the -lactam ring. When chiral ester enolates are used, asymmetric induction occurs to yield optically active -lactams with up to 60% ee. Synthetic and mechanistic details of these reactions are discussed. 1980, American Chemical Society. All rights reserved.

published proceedings

  • JOURNAL OF ORGANIC CHEMISTRY

altmetric score

  • 6

author list (cited authors)

  • GLUCHOWSKI, C., COOPER, L., BERGBREITER, D. E., & NEWCOMB, M.

citation count

  • 72

complete list of authors

  • GLUCHOWSKI, C||COOPER, L||BERGBREITER, DE||NEWCOMB, M

publication date

  • August 1980