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Decarboxylative Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbamates
Author(s) -
Dočekal Vojtěch,
Šimek Michal,
Dračínský Martin,
Veselý Jan
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803677
Subject(s) - allylic rearrangement , amination , enantioselective synthesis , chemistry , organocatalysis , organic chemistry , optically active , amine gas treating , catalysis , combinatorial chemistry
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.