2-Azabicyclo[2.2.1]hept-5-en-3-one: Chemical profile of a versatile synthetic building block and its impact on the development of therapeutics

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Abstract

A comprehensive account of the structural attributes and the progressive development of various methods of preparation of Vince lactam and the resolution of its stereoisomers is presented. Whiting and co-workers performed mechanistic investigation on the Diels-Alder reaction of tosyl cyanide and cyclopentadiene via labeling experiments. The proposal included the rearrangement of intermediate, to furnish the desired lactam along with the acetyl tosyl sulfinate side-product. Hongo et al. studied Lipase enzymes for similar resolution of racemic mixtures. Here, the transesterification of the substrate furnished preferential formation of the acyl derivative of one enantiomer. The versatility of Vince lactam is represented by the numerous transition metal catalyzed methodology development reactions which have used it as a model substrate of ample significance. In 2008, Abe and co-workers further extended Chan's work with copper mediated N-arylation and made Vince lactam the model substrate of choice for exploring this transformation.

Original languageEnglish (US)
Pages (from-to)4642-4686
Number of pages45
JournalChemical Reviews
Volume112
Issue number8
DOIs
StatePublished - Aug 8 2012

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