Carbamoyl Anion Addition to Azirines.

Autor: Kerner MJ; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States., Kuttruff CA; Medicinal Chemistry, Boehringer Ingelheim Pharma GmbH & Co KG, 88397 Biberach an der Riss, Germany., Chevliakov M; Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, Connecticut 06877, United States., Buono FG; Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, Connecticut 06877, United States., Gao DA; Material and Analytical Sciences, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, Connecticut 06877, United States., Krawiec M; Material and Analytical Sciences, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, Connecticut 06877, United States., Busacca CA; Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, Connecticut 06877, United States., Senanayake CH; Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, Connecticut 06877, United States., Wipf P; Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States., Reeves JT; Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, Connecticut 06877, United States.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2021 Jun 04; Vol. 23 (11), pp. 4396-4399. Date of Electronic Publication: 2021 May 14.
DOI: 10.1021/acs.orglett.1c01334
Abstrakt: The addition of carbamoyl anions to azirines affords synthetically useful 2-aziridinyl amide building blocks. The reaction scope was explored with respect to both formamide and azirine, and the addition was found to be highly diastereoselective. A one-pot conversion of a ketoxime to an aziridinyl amide was demonstrated. The method was employed to incorporate an aziridine residue into a dipeptide segment.
Databáze: MEDLINE