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Access to β‐Lactams by Enantioselective Palladium(0)‐Catalyzed C(sp 3 )H Alkylation
Author(s) -
Pedroni Julia,
Boghi Michele,
Saget Tanguy,
Cramer Nicolai
Publication year - 2014
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.201405508
Subject(s) - phosphoramidite , chemistry , enantioselective synthesis , catalysis , aryl , palladium , ring (chemistry) , combinatorial chemistry , ligand (biochemistry) , alkylation , stereochemistry , surface modification , organic synthesis , medicinal chemistry , organic chemistry , receptor , dna , biochemistry , alkyl , oligonucleotide
β‐Lactams are very important structural motifs because of their broad biological activities as well as their propensity to engage in ring‐opening reactions. Transition‐metal‐catalyzed CH functionalizations have emerged as strategy enabling yet uncommon highly efficient disconnections. In contrast to the significant progress of Pd 0 ‐catalyzed CH functionalization for aryl–aryl couplings, related reactions involving the formation of saturated C(sp 3 )C(sp 3 ) bonds are elusive. Reported here is an asymmetric CH functionalization approach to β‐lactams using readily accessible chloroacetamide substrates. Important aspects of this transformation are challenging C(sp 3 )C(sp 3 ) and strain‐building reductive eliminations to for the four‐membered ring. In general, the β‐lactams are formed in excellent yields and enantioselectivities using a bulky taddol phosphoramidite ligand in combination with adamantyl carboxylic acid as cocatalyst.