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An efficient “on water”-promoted direct catalytic vinylogous Henry reaction is described, giving products in excellent yields and diastereoselectivities.

Abstract:The direct asymmetric vinylogous Michael addition of 3,5-dialkyl-substituted 4-nitroisoxazoles with a,b-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.

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