3334-90-5Relevant academic research and scientific papers
Utilization of Cyclic Amides as Masked Aldehyde Equivalents in Reductive Amination Reactions
Prince, Robin J.,Gao, Fang,Pazienza, Jessica E.,Marx, Isaac E.,Schulz, Jurgen,Hopkins, Brian T.
, p. 7936 - 7949 (2019)
An operationally simple protocol has been discovered that couples primary or secondary amines with N-aryl-substituted lactams to deliver differentiated diamines in moderate to high yields. The process allows for the partial reduction of a lactam in the presence of Cp2ZrHCl (Schwartz's reagent), followed by a reductive amination between the resulting hemiaminal and primary or secondary amine. These reactions can be telescoped in a one-pot fashion to significantly simplify the operation. The scope of amines and substituted lactams of various ring sizes was demonstrated through the formation of a range of differentiated diamine products. Furthermore, this methodology was expanded to include N-aryl pyrrolidinone substrates with an enantiopure ester group at the 5-position, and α-amino piperidinones were prepared with complete retention of stereochemical information. The development of this chemistry has enabled the consideration of lactams as useful synthons.
