Palladium catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes: synthesis of alpha,alpha-disubstituted dihydropyrroles and studies towards an asymmetric protocol

Adele Faulkner; James S. Scott; John F. Bower

doi:10.1039/c2cc38944d

Palladium catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes: synthesis of alpha,alpha-disubstituted dihydropyrroles and studies towards an asymmetric protocol

Adele Faulkner, James S. Scott, John F. Bower^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

51 Citations (Scopus)

Abstract

We report efficient Pd-catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes as the basis of a general entry to alpha,alpha-disubstituted pyrrolidine derivatives. We also demonstrate that catalytic asymmetric variants of this chemistry are feasible by employing a suitable chiral ligand.

Original language	English
Pages (from-to)	1521-1523
Number of pages	3
Journal	Chemical Communications
Volume	49
Issue number	15
DOIs	https://doi.org/10.1039/c2cc38944d
Publication status	Published - 2013

Keywords

KETONE O-PENTAFLUOROBENZOYLOXIMES
HECK REACTIONS
ENANTIOSELECTIVE SYNTHESIS
AMMONIUM-SALTS
DERIVATIVES
REARRANGEMENT
INSERTION
ALKYNES
PHOSPHORAMIDITES
STEREOCENTERS

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3-month Core Capability for Chemistry Research
Crosby, J.
1/01/13 → 1/04/13
Project: Research
New Transition Metal Catalysed Methods for Alkyl C-N Bond Formation
Bower, J. F.
3/11/11 → 3/11/13
Project: Research

Cite this

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title = "Palladium catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes: synthesis of alpha,alpha-disubstituted dihydropyrroles and studies towards an asymmetric protocol",

abstract = "We report efficient Pd-catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes as the basis of a general entry to alpha,alpha-disubstituted pyrrolidine derivatives. We also demonstrate that catalytic asymmetric variants of this chemistry are feasible by employing a suitable chiral ligand.",

keywords = "KETONE O-PENTAFLUOROBENZOYLOXIMES, HECK REACTIONS, ENANTIOSELECTIVE SYNTHESIS, AMMONIUM-SALTS, DERIVATIVES, REARRANGEMENT, INSERTION, ALKYNES, PHOSPHORAMIDITES, STEREOCENTERS",

author = "Adele Faulkner and Scott, {James S.} and Bower, {John F.}",

year = "2013",

doi = "10.1039/c2cc38944d",

language = "English",

volume = "49",

pages = "1521--1523",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "15",

}

Palladium catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes: synthesis of alpha,alpha-disubstituted dihydropyrroles and studies towards an asymmetric protocol. / Faulkner, Adele; Scott, James S.; Bower, John F.

In: Chemical Communications, Vol. 49, No. 15, 2013, p. 1521-1523.

Research output: Contribution to journal › Article (Academic Journal) › peer-review

TY - JOUR

T1 - Palladium catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes: synthesis of alpha,alpha-disubstituted dihydropyrroles and studies towards an asymmetric protocol

AU - Faulkner, Adele

AU - Scott, James S.

AU - Bower, John F.

PY - 2013

Y1 - 2013

N2 - We report efficient Pd-catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes as the basis of a general entry to alpha,alpha-disubstituted pyrrolidine derivatives. We also demonstrate that catalytic asymmetric variants of this chemistry are feasible by employing a suitable chiral ligand.

AB - We report efficient Pd-catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes as the basis of a general entry to alpha,alpha-disubstituted pyrrolidine derivatives. We also demonstrate that catalytic asymmetric variants of this chemistry are feasible by employing a suitable chiral ligand.

KW - KETONE O-PENTAFLUOROBENZOYLOXIMES

KW - HECK REACTIONS

KW - ENANTIOSELECTIVE SYNTHESIS

KW - AMMONIUM-SALTS

KW - DERIVATIVES

KW - REARRANGEMENT

KW - INSERTION

KW - ALKYNES

KW - PHOSPHORAMIDITES

KW - STEREOCENTERS

U2 - 10.1039/c2cc38944d

DO - 10.1039/c2cc38944d

M3 - Article (Academic Journal)

C2 - 23321771

VL - 49

SP - 1521

EP - 1523

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 15

ER -

Palladium catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes: synthesis of alpha,alpha-disubstituted dihydropyrroles and studies towards an asymmetric protocol

Abstract

Keywords

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3-month Core Capability for Chemistry Research

New Transition Metal Catalysed Methods for Alkyl C-N Bond Formation

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