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

altmetric score

  • 6

author list (cited authors)

  • Gluchowski, C., Cooper, L., Bergbreiter, D. E., & Newcomb, M.

citation count

  • 68

publication date

  • August 1980