Abstract
Seebach's synthetic method of self-regeneration of stereocenters “SRS” has been applied to the addition reaction of diphenylimine 1 to the lithium enolates of (2 S,5 S)-2-( tert-butyl)-5-methyl-1,3-dioxolan-4-one 2a and of (2 S,5 S)-2-( tert-butyl)-5-phenyl-1,3-dioxolan-4-one 2b. Variable sol4S 4R mixtures of (3 R)-3-hydroxy-β-lactams 4a,b are obtained, depending on the reaction conditions. The induced enantioselectivity ( ee) is very high, and the simple selectivity (exo-endo) is low. Overall, this appears a rather direct approach to chiral β-lactams with full control of stereochemistry at C3. The stereoselective radical reduction of the stereoisomer (3R,4R)-E- 4a afforded the homochiral C3,C4-monosubstituted β-lactam (3S,4S)-Z- 10 .
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