Synthesis of β-Lactams by Palladium(0)-Catalyzed C(sp3 )-H Carbamoylation

Angewandte Chemie
David DaillerOlivier Baudoin

Abstract

A general and user-friendly synthesis of β-lactams is reported that makes use of Pd0 -catalyzed carbamoylation of C(sp3 )-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(sp3 )-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.

References

Dec 9, 2003·Angewandte Chemie·Olivier BaudoinFrançoise Guéritte
Nov 24, 2005·Angewandte Chemie·Stefan KlausMatthias Beller
Dec 31, 2005·Chemistry : a European Journal·Eniko Forró, Ferenc Fülöp
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Oct 22, 2008·Journal of the American Chemical Society·Manon ChaumontetOlivier Baudoin
Aug 5, 2010·Journal of the American Chemical Society·Sophie RousseauxOlivier Baudoin
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Mar 13, 2012·Chemistry : a European Journal·Nicolas MartinOlivier Baudoin
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Citations

Jul 3, 2018·Angewandte Chemie·Christopher G NewtonNicolai Cramer
Jul 25, 2019·Angewandte Chemie·Kankanala RamakrishnaDebabrata Maiti
Jul 15, 2017·Angewandte Chemie·Jaime R Cabrera-PardoMatthew J Gaunt
Aug 23, 2019·Chemistry : a European Journal·Matteo VirelliLutz Ackermann
Mar 3, 2020·Chemistry : a European Journal·Riccardo SalvioMarco Bella
Feb 20, 2020·Chemistry : a European Journal·Kanako Nozawa-KumadaYoshinori Kondo
Aug 9, 2020·Chemistry : a European Journal·Oleksandr VyhivskyiOlivier Baudoin
Mar 13, 2021·Organic & Biomolecular Chemistry·Joseph D Gbubele, Tomasz K Olszewski
Aug 24, 2017·Journal of the American Chemical Society·Julia Pedroni, Nicolai Cramer
Jul 20, 2019·The Journal of Organic Chemistry·Romain MelotOlivier Baudoin
May 16, 2019·The Journal of Organic Chemistry·Riccardo SalvioMarco Bella
Nov 11, 2020·Journal of the American Chemical Society·Yue LiMengchun Ye
Feb 18, 2020·Chemical Reviews·Aaron TrowbridgeMatthew J Gaunt
Oct 26, 2021·Chemical Communications : Chem Comm·Sumeet Ranjan SahooDebabrata Maiti

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