Access to beta-Lactams by Enantioselective Palladium(0)-Catalyzed C(sp(3))-H Alkylation

beta-Lactams are very important structural motifs because of their broad biological activities as well as their propensity to engage in ring-opening reactions. Transitionmetal- catalyzed C-H functionalizations have emerged as strategy enabling yet uncommon highly efficient disconnections. In contrast to the significant progress of Pd-0-catalyzed C-H 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 C-H functionalization approach to beta-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 blactams are formed in excellent yields and enantioselectivities using a bulky taddol phosphoramidite ligand in combination with adamantyl carboxylic acid as cocatalyst.


Published in:
Angewandte Chemie-International Edition, 53, 34, 9064-9067
Year:
2014
Publisher:
Weinheim, Wiley-Blackwell
ISSN:
1433-7851
Keywords:
Laboratories:




 Record created 2014-10-23, last modified 2018-09-13


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