Phase Transfer Catalysed Asymmetric Aza-Henry Reaction using N-Carbamoyl Imines Generated in Situ from alfa-Amido Sulfones

Francesco Fini, Valentina Sgarzani, Daniel Pettersen, Raquel P. Herrera, Luca Bernardi, Alfredo Ricci. Phase Transfer Catalysed Asymmetric Aza-Henry Reaction using N-Carbamoyl Imines Generated in Situ from alfa-Amido Sulfones. Angew. Chem. Int. Ed. . 2005, Vol. 44 / 2005, p. 7975-2005.

<p>A new catalytic enantioselective aza-Henry reaction was developed. A commercially available phase transfer catalyst, in combination with a base, was able to promote the formation of N-carbamoyl imines in situ from a-amido sulfones, and to activate nitromethane for the asymmetric addition, furnishing N-carbamoyl protected a-nitroamines in fairly good yields and with up to 98% ee.</p>