We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Iridium-Catalyzed Reductive Strecker Reaction for Late-Stage Amide and Lactam Cyanation.
- Authors
Fuentes De Arriba, Ángel L.; Lenci, Elena; Sonawane, Mahendra; Formery, Odilon; Dixon, Darren J.
- Abstract
A new iridium-catalyzed reductive Strecker reaction for the direct and efficient formation of α-amino nitrile products from a broad range of (hetero)aromatic and aliphatic tertiary amides, and N-alkyl lactams is reported. The protocol exploits the mild and highly chemoselective reduction of the amide and lactam functionalities using IrCl(CO)[P(C6H5)3]2 (Vaska's complex) in the presence of tetramethyldisiloxane, as a reductant, to directly generate hemiaminal species able to undergo substitution by cyanide upon treatment with TMSCN (TMS=trimethylsilyl). The protocol is simple to perform, broad in scope, efficient (up to 99 % yield), and has been successfully applied to the late-stage functionalization of amide- and lactam-containing drugs, and naturally occurring alkaloids, as well as for the selective cyanation of the carbonyl carbon atom linked to the N atom of proline residues within di- and tripeptides.
- Subjects
IRIDIUM catalysts; CHEMOSELECTIVITY; LACTAMS; AMIDES; NITRILE synthesis
- Publication
Angewandte Chemie International Edition, 2017, Vol 56, Issue 13, p3655
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201612367