Organocatalyzed Asymmetric Vinylogous Michael Reactions of 3,5‐Dialkyl‐Substituted 4‐Nitroisoxazoles: A Direct Method for the Synthesis of Chiral Isoxazole Derivatives

Publisher: John Wiley & Sons Inc

E-ISSN: 1615-4169|357|6|1299-1304

ISSN: 1615-4150

Source: ADVANCED SYNTHESIS & CATALYSIS, Vol.357, Iss.6, 2015-04, pp. : 1299-1304

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Abstract

AbstractThe direct asymmetric vinylogous Michael addition of 3,5‐dialkyl‐substituted 4‐nitroisoxazoles with α,β‐unsaturated aldehydes catalyzed by a diphenylprolinol TBS ether organocatalyst is described, giving products with moderate to good yields and up to excellent enantioselectivities (96% ee). This approach provides an easy access to highly functionalized chiral isoxazole derivatives.