Highly Z-selective synthesis of α,β-unsaturated amides with the Peterson reaction between α-silylamides and aldehydesElectronic supplementary information (ESI) available: synthesis and characterisation data for 1a,b and 3a–i. See http://www.rsc.org/suppdata/cc/b0/b004416o/

Abstract

The Peterson reaction of triphenylsilylacetamide Ph₃SiCH₂CONBn₂ with aromatic aldehydes and certain aliphatic aldehydes proceeded to give the corresponding α,β-unsaturated amide with high Z selectivity (up to Z∶E = >97∶<3).