A straightforward stereoselective and entantiodivergent cyclization strategy for the construction of d-lactams is presented. Recently, we have reported a cyclization strategy, which makes use of chiral malonic esters prepared from enantiomerically enriched mono esters of disubstituted malonic acid (scheme). The cyclization occurs with the selective displacement of a substituted benzyl alcohol as the leaving group. The resulting d-lactam can be readily converted into a novel nipecotic acid analogue. Nipecotic acid has been shown to be a GABA reuptake inhibitor. To the best of our knowledge, there has been no optically enriched synthesis of this compound reported in the literature to date. Our strategy overcomes this challenge by utilizing straightforward synthetic manipulations from readily available materials.

Stereodivergent strategy for the preparation of δ-lactams and their use in the synthesis of a nipecotic acid analog

245th National Meeting (2013)

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