A general approach to the catalytic asymmetric aza-Henry reaction has been developed. The combination of a commercially available phase-transfer catalyst (PTC) with a base is able to promote the in situ formation of N-carbamoyl imines from α-amido sulfones and activate nitromethane towards the asymmetric addition reaction, thus furnishing N-carbamoyl-protected β-nitroamines in good yields and with up to 98 % ee (see scheme; PG=protecting group).
Phase-Transfer-Catalyzed Asymmetric Aza-Henry Reaction Using N-Carbamoyl Imines Generated In Situ from alpha-Amido Sulfones / Fini, Francesco; Sgarzani, Valentina; Pettersen, Daniel; Herrera, Raquel P.; Bernardi, Luca; Ricci, Alfredo. - In: ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. - ISSN 1433-7851. - STAMPA. - 44:48(2005), pp. 7975-7978. [10.1002/anie.200502646]
Phase-Transfer-Catalyzed Asymmetric Aza-Henry Reaction Using N-Carbamoyl Imines Generated In Situ from alpha-Amido Sulfones
FINI, Francesco;
2005
Abstract
A general approach to the catalytic asymmetric aza-Henry reaction has been developed. The combination of a commercially available phase-transfer catalyst (PTC) with a base is able to promote the in situ formation of N-carbamoyl imines from α-amido sulfones and activate nitromethane towards the asymmetric addition reaction, thus furnishing N-carbamoyl-protected β-nitroamines in good yields and with up to 98 % ee (see scheme; PG=protecting group).
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