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Synthesis of β-Substituted α-Amino Acids via Lewis Acid Promoted Radical Conjugate Additions to α,β-Unsaturated α-Nitro Esters and Amides
Srikanth,Castle, Steven L.
, p. 449 - 452 (2007/10/03)
(Martix presented) β-Substituted α,β-unsaturated α-nitro esters and amides undergo radical conjugate additions when treated with an appropriate Lewis acid. Deuterium studies revealed that the acidic α-stereocenter of the α-nitro ester products does not racemize under strictly controlled workup conditions. The α-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 β-substituted α-amino acids in two simple steps.
