PREPARATION OF BETA-LACTAMS BY THE CONDENSATION OF LITHIUM ESTER ENOLATES WITH ARYL ALDIMINES
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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.