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

doi:10.1021/acs.joc.0c00575

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 Journal › Article › Academic › peer-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 language	English
Pages (from-to)	9566-9584
Number of pages	19
Journal	Journal of Organic Chemistry
Volume	85
Issue number	15
Early online date	25 Jun 2020
DOIs	https://doi.org/10.1021/acs.joc.0c00575
Publication status	Published - 7 Aug 2020

Funding

This work was financially supported by the Netherlands Organisation for Scientific Research (NWO). We thank Daniel Preschel for HRMS measurements and Elwin Janssen for the NMR support (both Vrije Universiteit Amsterdam). We thank SURFsara for the use of the Cartesius and Lisa supercomputer. Dr. Christophe Vande Velde (University of Antwerp) is gratefully acknowledged for X-ray crystallographic measurements and solving the structure of cis - 6s . We also thank Prof. Kristof Van Hecke (Ghent University) for providing diffractometer time, and the Hercules Foundation (project AUGE/11/029 “3D-SPACE: 3D Structural Platform Aiming for Chemical Excellence”) for funding of the diffractometer.

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10.1021/acs.joc.0c00575

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title = "Diastereoselective Synthesis of β-Lactams by Ligand-Controlled Stereodivergent Intramolecular Tsuji-Trost Allylation",

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.",

author = "Matteo Faltracco and Verena Sukowski and \{Van Druenen\}, Max and Hamlin, \{Trevor A.\} and Bickelhaupt, \{F. Matthias\} and Eelco Ruijter",

year = "2020",

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doi = "10.1021/acs.joc.0c00575",

language = "English",

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journal = "Journal of Organic Chemistry",

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T1 - Diastereoselective Synthesis of β-Lactams by Ligand-Controlled Stereodivergent Intramolecular Tsuji-Trost Allylation

AU - Faltracco, Matteo

AU - Sukowski, Verena

AU - Van Druenen, Max

AU - Hamlin, Trevor A.

AU - Bickelhaupt, F. Matthias

AU - Ruijter, Eelco

PY - 2020/8/7

Y1 - 2020/8/7

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85090029517

UR - https://www.scopus.com/pages/publications/85090029517#tab=citedBy

U2 - 10.1021/acs.joc.0c00575

DO - 10.1021/acs.joc.0c00575

M3 - Article

AN - SCOPUS:85090029517

SN - 0022-3263

VL - 85

SP - 9566

EP - 9584

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

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

Abstract

Funding

UN SDGs

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CCDC 1957914: Experimental Crystal Structure Determination

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

Abstract

Funding

UN SDGs

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Other files and links

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CCDC 1957914: Experimental Crystal Structure Determination

Cite this