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).
Fini F, Sgarzani V, Pettersen D, Herrera R P, Bernardi L, Ricci A (2005). PHASE TRANSFER CATALYSED ASYMMETRIC AZA-HENRY REACTION USING N-CARBAMOYL IMINES GENERATED IN SITU FROM ALFA-AMIDO SULFONES. ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, 44, 7975-7978 [10.1002/anie.200502646].
PHASE TRANSFER CATALYSED ASYMMETRIC AZA-HENRY REACTION USING N-CARBAMOYL IMINES GENERATED IN SITU FROM ALFA-AMIDO SULFONES.
FINI, FRANCESCO;BERNARDI, LUCA;RICCI, ALFREDO MARCO
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).I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
