Access to β‐Lactams by Enantioselective Palladium(0)‐Catalyzed C(sp3)H Alkylation1. Issue 34 (1st July 2014)

• Record Type: Journal Article
• Authors: Pedroni, Julia; Boghi, Michele; Saget, Tanguy; Cramer, Nicolai
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 34(2014)
• Page Start: 9064
• Page End: 9067
• Publication Date: 2014-07-01
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201405508
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 CH functionalizations have emerged as strategy enabling yet uncommon highly efficient disconnections. In contrast to the significant progress of Pd⁰‐catalyzed CH functionalization for aryl–aryl couplings, related reactions involving the formation of saturated C(sp³)C(sp³) bonds are elusive. Reported here is an asymmetric CH functionalization approach to β‐lactams using readily accessible chloroacetamide substrates. Important aspects of this transformation are challenging C(sp³)C(sp³) 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.</p> </abstract>