We and others have demonstrated the utility of the permanganate-promoted oxidative cyclization of 1,5-dienes for synthesis of structural fragments found in oxygenated natural productsla'b•2 and materials of medicinal importance.3 In the standard implementation of this reaction, a structurally complex product possessing four new tetrahedral stereocenters is created stereospecifically from a simple achiral diene precursor in a single transformation. Of course under these circumstances racemic
AnEfficient Asymmetric Synthesis of (3S)-3-Amino-1-(4cyanophenyl)-2-oxopyrrolidine Hydrochloride Salt.-Coupling of bromide (II) with nitrile (III) and subsequent cyclization gives the lactam ring of the title compound. Displacement of the bromide in intermediate (IV) by treatment with excess NH 4 OH and work-up of the racemic amine with (R)-mandelic acid (V) leads to isolation of the racemic (R)-mandelic acid salt (VI). The optically pure title compound is then obtained through the dynamic resolution of amine (VI) in the presence of a catalytic amount of salicyl aldehyde and (R)-mandelic acid. -(COLSON, P.-J.; PRZYBYLA, C. A.; WISE, B. E.; BABIAK, K. A.; SEANEY, L. M.; KORTE, D. E.; Tetrahedron: Asymmetry 9 (1998) 15, 2587-2593; Monsato Life Sci., Searle, Synth. Dev., Skokie, IL 60077, USA; EN)
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