Decarboxylative Organocatalytic Allylic Amination of Morita-Baylis-Hillman Carbamates

0494023 - ÚOCHB 2019 RIV DE eng J - Článek v odborném periodiku
Dočekal, V. - Šimek, M. - Dračínský, Martin - Veselý, J.
Decarboxylative Organocatalytic Allylic Amination of Morita-Baylis-Hillman Carbamates.
Chemistry - A European Journal. Roč. 24, č. 51 (2018), s. 13441-13445. ISSN 0947-6539. E-ISSN 1521-3765
Grant CEP: GA ČR(CZ) GA18-11851S
Institucionální podpora: RVO:61388963
Klíčová slova: allylic compounds * Brønsted acid * chirality * cinchona alkaloids * enantioselective allylic amination
Obor OECD: Organic chemistry
Impakt faktor: 5.160, rok: 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 Bronsted 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 alpha-methylene beta-lactams, and other optically active beta-lactams, such as the cholesterol-lowering drug Ezetimibe.
Trvalý link: http://hdl.handle.net/11104/0287270