Abstract
[reaction: see text] Beta-substituted alpha,beta-unsaturated alpha-nitro esters and amides undergo radical conjugate additions when treated with an appropriate Lewis acid. Deuterium studies revealed that the acidic alpha-stereocenter of the alpha-nitro ester products does not racemize under strictly controlled workup conditions. The alpha-nitro amides did racemize significantly during chromatography, but this could be greatly minimized by subjecting the crude adducts to subsequent transformations. The conjugate addition products can be elaborated into beta-substituted alpha-amino acids in two simple steps.
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