Metal-Free Stereoselective Synthesis of ( E )- and ( Z )-N-Monosubstituted β-Aminoacrylates via Condensation Reactions of Carbamates.

Autor: Pollack SR; Department of Process Research & Development, MRL, Merck & Co., Inc., Rahway, New Jersey 07065, United States., Dion A; Department of Process Research & Development, MRL, Merck & Co., Inc., Rahway, New Jersey 07065, United States.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2021 Sep 03; Vol. 86 (17), pp. 11748-11762. Date of Electronic Publication: 2021 Aug 16.
DOI: 10.1021/acs.joc.1c01212
Abstrakt: N-monosubstituted β-aminoacrylates are building blocks, which have been used in the preparation of amino acids and pharmaceuticals. Two efficient, stereoselective methods of preparation, via acid- or base-promoted condensation reactions of carbamates, are described. The base-promoted reaction is E -selective, while acid catalysis can, through the choice of solvent, selectively form E or Z . The acid-catalyzed E -selective process proceeds through a crystallization obviating the need for chromatographic purification.
Databáze: MEDLINE