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

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

Pedroni, Julia  
•
Boghi, Michele  
•
Saget, Tanguy  
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2014
Angewandte Chemie International Edition

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.

  • Details
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Type
research article
DOI
10.1002/anie.201405508
Web of Science ID

WOS:000340526400043

Author(s)
Pedroni, Julia  
Boghi, Michele  
Saget, Tanguy  
Cramer, Nicolai  
Date Issued

2014

Publisher

Wiley-Blackwell

Published in
Angewandte Chemie International Edition
Volume

53

Issue

34

Start page

9064

End page

9067

Subjects

asymmetric catalysis

•

C-H activation

•

cross coupling

•

lactams

•

palladium

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LCSA  
Available on Infoscience
October 23, 2014
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/107774
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