Matteo Faltracco1, Verena Sukowski1, Max van Druenen1, Trevor A Hamlin2, F Matthias Bickelhaupt2,3, Eelco Ruijter1. 1. Department of Chemistry & Pharmaceutical Sciences, Amsterdam Institute of Molecular and Life Sciences (AIMMS), Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081 HZ Amsterdam, The Netherlands. 2. Department of Theoretical Chemistry, Amsterdam Institute of Molecular and Life Sciences (AIMMS), Amsterdam Center for Multiscale Modeling (ACMM), Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands. 3. Institute for Molecules and Materials, Radboud University, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
Abstract
The diastereoselective synthesis of highly substituted β-lactams by intramolecular Tsuji-Trost allylation is reported. Judicious selection of the ligand on palladium allows selective access to either the trans isomer (in generally good to excellent yield with very high diastereomeric excess) or cis isomer (with yields and diastereoselectivity ranging from modest to excellent depending on the substrate). The reaction proceeds under exceedingly mild conditions (rt, no additives) with a broad range of substrates, which are readily accessible by the Ugi reaction.
The diastereoselective synthesis of highly substituted β-lactams by intramolecular Tsuji-Trost allylation is reported. Judicious selection of the ligand on palladium allon class="Chemical">ws selective access to either the trans isomer (in generally good to excellent yield with very high diastereomeric excess) or cis isomer (with yields and diastereoselectivity ranging from modest to excellent depending on the substrate). The reaction proceeds under exceedingly mild conditions (rt, no additives) with a broad range of substrates, which are readily accessible by the Ugi reaction.
Authors: Matteo Faltracco; Koen N A van de Vrande; Martijn Dijkstra; Jordy M Saya; Trevor A Hamlin; Eelco Ruijter Journal: Angew Chem Int Ed Engl Date: 2021-05-26 Impact factor: 15.336