Decarboxylative Organocatalytic Allylic Amination of Morita-Baylis-Hillman Carbamates.

Vojtěch Dočekal Michal Šimek Martin Dračínský Jan Veselý

Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2018)

The present study reports the organocatalytic enantioselective allylic amination of Morita-Baylis-Hillman carbamates efficiently catalyzed by a chiral amine in the presence of a Brønsted acid. Chiral allylic amines were produced in high yields (up to 98 %) and enantioselectivities (up to 97 % ee). This method provides an efficient and easily performed route to prepare α-methylene-β-lactams, and other optically active β-lactams, such as the cholesterol-lowering drug Ezetimibe.

Keyphrases

capillary electrophoresis
ionic liquid
adverse drug
room temperature
emergency department
mass spectrometry
low density lipoprotein
visible light