Synthesis of highly substituted pyrrolidines via palladium-catalyzed cyclization of 5-vinyloxazolidinones and activated alkenes

Julian G. Knight; Paul A. Stoker; Kirill Tchabanenko; Simon J. Harwood; Kenneth W. M. Lawrie

doi:10.1016/j.tet.2008.02.019

Synthesis of highly substituted pyrrolidines via palladium-catalyzed cyclization of 5-vinyloxazolidinones and activated alkenes

Julian G. Knight, Paul A. Stoker, Kirill Tchabanenko, Simon J. Harwood, Kenneth W. M. Lawrie

School of Chemistry and Chemical Engineering

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

29 Citations (Scopus)

Abstract

N-Tosyl-5,5-divinyloxazolidin-2-one undergoes a palladium-catalyzed decarboxylative cyclization across a range of electrophilic alkenes to give the corresponding pyrrolidine derivatives bearing two contiguous quaternary centres. Alkenes bearing two electron-withdrawing groups are required; pyrrolidines were not formed from mono-activated alkenes. Bulky, electron-rich phosphines promote pyrrolidine formation with less highly electrophilic, doubly activated alkenes, and a dramatic improvement is observed in the presence of iodide.

Original language	English
Pages (from-to)	3744-3750
Number of pages	7
Journal	Tetrahedron
Volume	64
Issue number	17
DOIs	https://doi.org/10.1016/j.tet.2008.02.019
Publication status	Published - 21 Apr 2008

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10.1016/j.tet.2008.02.019

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title = "Synthesis of highly substituted pyrrolidines via palladium-catalyzed cyclization of 5-vinyloxazolidinones and activated alkenes",

abstract = "N-Tosyl-5,5-divinyloxazolidin-2-one undergoes a palladium-catalyzed decarboxylative cyclization across a range of electrophilic alkenes to give the corresponding pyrrolidine derivatives bearing two contiguous quaternary centres. Alkenes bearing two electron-withdrawing groups are required; pyrrolidines were not formed from mono-activated alkenes. Bulky, electron-rich phosphines promote pyrrolidine formation with less highly electrophilic, doubly activated alkenes, and a dramatic improvement is observed in the presence of iodide.",

author = "Knight, {Julian G.} and Stoker, {Paul A.} and Kirill Tchabanenko and Harwood, {Simon J.} and Lawrie, {Kenneth W. M.}",

year = "2008",

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T1 - Synthesis of highly substituted pyrrolidines via palladium-catalyzed cyclization of 5-vinyloxazolidinones and activated alkenes

AU - Knight, Julian G.

AU - Stoker, Paul A.

AU - Tchabanenko, Kirill

AU - Harwood, Simon J.

AU - Lawrie, Kenneth W. M.

PY - 2008/4/21

Y1 - 2008/4/21

N2 - N-Tosyl-5,5-divinyloxazolidin-2-one undergoes a palladium-catalyzed decarboxylative cyclization across a range of electrophilic alkenes to give the corresponding pyrrolidine derivatives bearing two contiguous quaternary centres. Alkenes bearing two electron-withdrawing groups are required; pyrrolidines were not formed from mono-activated alkenes. Bulky, electron-rich phosphines promote pyrrolidine formation with less highly electrophilic, doubly activated alkenes, and a dramatic improvement is observed in the presence of iodide.

AB - N-Tosyl-5,5-divinyloxazolidin-2-one undergoes a palladium-catalyzed decarboxylative cyclization across a range of electrophilic alkenes to give the corresponding pyrrolidine derivatives bearing two contiguous quaternary centres. Alkenes bearing two electron-withdrawing groups are required; pyrrolidines were not formed from mono-activated alkenes. Bulky, electron-rich phosphines promote pyrrolidine formation with less highly electrophilic, doubly activated alkenes, and a dramatic improvement is observed in the presence of iodide.

U2 - 10.1016/j.tet.2008.02.019

DO - 10.1016/j.tet.2008.02.019

M3 - Article

SN - 0040-4020

VL - 64

SP - 3744

EP - 3750

JO - Tetrahedron

JF - Tetrahedron

IS - 17

ER -

Synthesis of highly substituted pyrrolidines via palladium-catalyzed cyclization of 5-vinyloxazolidinones and activated alkenes

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