Synthesis of Strained γ-Lactams by Palladium(0)-Catalyzed C(sp3)-H Alkenylation and Application to Alkaloid Synthesis

Philipp M. Holstein; David Dailler; Julien Vantourout; Janah Shaya; Anthony Millet; Olivier Baudoin

doi:10.1002/anie.201511457

Synthesis of Strained γ-Lactams by Palladium(0)-Catalyzed C(sp³)-H Alkenylation and Application to Alkaloid Synthesis

Philipp M. Holstein, David Dailler, Julien Vantourout, Janah Shaya, Anthony Millet, Olivier Baudoin

Chemistry

Research output: Contribution to journal › Article › peer-review

53 Scopus citations

Abstract

A variety of strained α-alkylidene-γ-lactams were synthesized by palladium(0)-catalyzed intramolecular C(sp³)-H alkenylation from easily accessible acyclic and monocyclic bromoalkene precursors. These lactams are valuable intermediates for accessing various classes of mono- and bicylic alkaloids containing a pyrrolidine ring, as illustrated with the synthesis of an advanced model of the marine natural product plakoridine A and of the indolizidine alkaloid δ-coniceine.

Original language	British English
Pages (from-to)	2805-2809
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	8
DOIs	https://doi.org/10.1002/anie.201511457
State	Published - 18 Feb 2016

Keywords

C-C coupling
C-H activation
natural products
nitrogen heterocycles
palladium

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abstract = "A variety of strained α-alkylidene-γ-lactams were synthesized by palladium(0)-catalyzed intramolecular C(sp3)-H alkenylation from easily accessible acyclic and monocyclic bromoalkene precursors. These lactams are valuable intermediates for accessing various classes of mono- and bicylic alkaloids containing a pyrrolidine ring, as illustrated with the synthesis of an advanced model of the marine natural product plakoridine A and of the indolizidine alkaloid δ-coniceine.",

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AU - Holstein, Philipp M.

AU - Dailler, David

AU - Vantourout, Julien

AU - Shaya, Janah

AU - Millet, Anthony

AU - Baudoin, Olivier

PY - 2016/2/18

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AB - A variety of strained α-alkylidene-γ-lactams were synthesized by palladium(0)-catalyzed intramolecular C(sp3)-H alkenylation from easily accessible acyclic and monocyclic bromoalkene precursors. These lactams are valuable intermediates for accessing various classes of mono- and bicylic alkaloids containing a pyrrolidine ring, as illustrated with the synthesis of an advanced model of the marine natural product plakoridine A and of the indolizidine alkaloid δ-coniceine.

KW - C-C coupling

KW - C-H activation

KW - natural products

KW - nitrogen heterocycles

KW - palladium

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Synthesis of Strained γ-Lactams by Palladium(0)-Catalyzed C(sp³)-H Alkenylation and Application to Alkaloid Synthesis

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Keywords

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