Diastereoselective Synthesis of β-Lactams by Ligand-Controlled Stereodivergent Intramolecular Tsuji-Trost Allylation

Matteo Faltracco, Verena Sukowski, Max Van Druenen, Trevor A. Hamlin, F. Matthias Bickelhaupt, Eelco Ruijter*

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

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.

Original languageEnglish
Pages (from-to)9566-9584
Number of pages19
JournalJournal of Organic Chemistry
Volume85
Issue number15
Early online date25 Jun 2020
DOIs
Publication statusPublished - 7 Aug 2020

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