Decarboxylative Umpolung Synthesis of Amines from Carbonyl Compounds

2-Azaallyl anions are valuable intermediates which have versatile applications in functionalization with various electrophiles. Decarboxylation of the imines formed from aromatic aldehydes and alpha,alpha-diphenylglycine provides an interesting and efficient way to generate delocalized 2-azaallyl anions, which display high reactivity toward different electrophiles with excellent regioselectivity at the diphenylketimino aryl carbon of the 2-azaallyl anions. The transformation produces various amines in good yields under very mild conditions. This Synpacts article highlights the recent advances on the decarboxylative umpolung synthesis of amines from carbonyl compounds. 1 Introduction 2 Decarboxylative Umpolung Reactions of Carbonyl Compounds with Different Electrophiles 2.1 Reaction with pi-Allyl-Pd(II) Species 2.2 Reaction with Morita-Baylis-Hillman Adducts 2.3 Reaction with Imines 2.3.1 Intermolecular Reaction withN-Ts Imines 2.3.2 Intramolecular Reaction with ChiralN-tert-Butanesulfinyl Imines 2.4 Reaction with Aldehydes and Ketones 3 Decarboxylative Umpolung Reaction of alpha,beta-Unsaturated Aldehydes with Aldehydes \ 4 Conclusion