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Synthesis of β‐Lactams by Palladium(0)‐Catalyzed C(sp 3 )−H Carbamoylation
Author(s) -
Dailler David,
Rocaboy Ronan,
Baudoin Olivier
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201703109
Subject(s) - enantiopure drug , catalysis , palladium , enantioselective synthesis , carbon monoxide , chemistry , ligand (biochemistry) , stoichiometry , combinatorial chemistry , stereochemistry , organic chemistry , medicinal chemistry , receptor , biochemistry
A general and user‐friendly synthesis of β‐lactams is reported that makes use of Pd 0 ‐catalyzed carbamoylation of C(sp 3 )−H bonds, and operates under stoichiometric carbon monoxide in a two‐chamber reactor. This reaction is compatible with a range of primary, secondary and activated tertiary C−H bonds, in contrast to previous methods based on C(sp 3 )−H activation. In addition, the feasibility of an enantioselective version using a chiral phosphonite ligand is demonstrated. Finally, this method can be employed to synthesize valuable enantiopure free β‐lactams and β‐amino acids.