Remote Control of the C??3–C??4 Double??Bond Epoxidation of a Chiral 1, 2??Dihydroquinoline: Application to the Synthesis of (–)??(R)??Sumanirole (PNU??95666E)

L Jean??Gérard, F Macé, AN Ngo…

Index: Jean-Gerard, Ludivine; MacE, Frederic; Ngo, Anh Ngoc; Pauvert, Mickael; Dentel, Helene; Evain, Michel; Collet, Sylvain; Guingant, Andre European Journal of Organic Chemistry, 2012 , # 22 p. 4240 - 4248

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Citation Number: 2

Abstract

Abstract A twelve-step synthesis of (–)-(R)-sumanirole starting from quinoline is described. The first synthetic approach, using a chiral Reissert adduct, was too problematic to be pursued further. In the second successful approach, the authors took advantage of the stereoselective epoxidation of a 1, 2-dihydroquinoline bearing an Evans' chiral auxiliary at N- 1.