Enantioselective Narasaka-Heck Cyclizations: Synthesis of Tetrasubstituted Nitrogen-Bearing Stereocenters

Nicholas Race; Adele Faulkner; Gabriele Fumagalli; Takayuki Yamauchi; James S. Scott; Rydén-Landergren, Marie; Hazel Sparkes; John Bower

doi:10.1039/C6SC04466B

Enantioselective Narasaka-Heck Cyclizations: Synthesis of Tetrasubstituted Nitrogen-Bearing Stereocenters

Nicholas Race, Adele Faulkner, Gabriele Fumagalli, Takayuki Yamauchi, James S. Scott, Rydén-Landergren, Marie, Hazel Sparkes, John Bower

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Abstract

The first examples of highly enantioselective Narasaka-Heck cyclizations are described. A SPINOL-derived P,N-ligand system enables Pd-catalyzed 5-exo cyclization of a range of oxime esters with sterically diverse trisubstituted alkenes to generate dihydropyrroles containing tetrasubstituted nitrogen-bearing stereocenters in 56 to 86% yield and 90:10 to 95:5 e.r.. These processes are rare examples of reactions that proceed via enantioselective migratory insertion of alkenes into Pd-N bonds, and the first where trisubstituted alkenes are used to generate tetrasubstituted stereocenters with high enantioselectivity.

Original language	English
Pages (from-to)	1981-1985
Number of pages	5
Journal	Chemical Science
Volume	8
Issue number	3
Early online date	24 Nov 2016
DOIs	https://doi.org/10.1039/C6SC04466B
Publication status	Published - 1 Mar 2017

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10.1039/C6SC04466B

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A 13C NMR Coldprobe to Underpin Chemistry Research.
Butts, C. P.
28/02/14 → 29/11/17
Project: Research
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

Dr Hazel A Sparkes
- hazel.sparkesbristol.acuk
- School of Chemistry - Research Fellow in X-Ray Crystallography
Person: Academic

Cite this

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title = "Enantioselective Narasaka-Heck Cyclizations: Synthesis of Tetrasubstituted Nitrogen-Bearing Stereocenters",

abstract = "The first examples of highly enantioselective Narasaka-Heck cyclizations are described. A SPINOL-derived P,N-ligand system enables Pd-catalyzed 5-exo cyclization of a range of oxime esters with sterically diverse trisubstituted alkenes to generate dihydropyrroles containing tetrasubstituted nitrogen-bearing stereocenters in 56 to 86% yield and 90:10 to 95:5 e.r.. These processes are rare examples of reactions that proceed via enantioselective migratory insertion of alkenes into Pd-N bonds, and the first where trisubstituted alkenes are used to generate tetrasubstituted stereocenters with high enantioselectivity.",

author = "Nicholas Race and Adele Faulkner and Gabriele Fumagalli and Takayuki Yamauchi and Scott, {James S.} and Ryd{\'e}n-Landergren, Marie and Hazel Sparkes and John Bower",

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doi = "10.1039/C6SC04466B",

language = "English",

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T1 - Enantioselective Narasaka-Heck Cyclizations

T2 - Synthesis of Tetrasubstituted Nitrogen-Bearing Stereocenters

AU - Race, Nicholas

AU - Faulkner, Adele

AU - Fumagalli, Gabriele

AU - Yamauchi, Takayuki

AU - Scott, James S.

AU - Marie, Rydén-Landergren,

AU - Sparkes, Hazel

AU - Bower, John

PY - 2017/3/1

Y1 - 2017/3/1

N2 - The first examples of highly enantioselective Narasaka-Heck cyclizations are described. A SPINOL-derived P,N-ligand system enables Pd-catalyzed 5-exo cyclization of a range of oxime esters with sterically diverse trisubstituted alkenes to generate dihydropyrroles containing tetrasubstituted nitrogen-bearing stereocenters in 56 to 86% yield and 90:10 to 95:5 e.r.. These processes are rare examples of reactions that proceed via enantioselective migratory insertion of alkenes into Pd-N bonds, and the first where trisubstituted alkenes are used to generate tetrasubstituted stereocenters with high enantioselectivity.

AB - The first examples of highly enantioselective Narasaka-Heck cyclizations are described. A SPINOL-derived P,N-ligand system enables Pd-catalyzed 5-exo cyclization of a range of oxime esters with sterically diverse trisubstituted alkenes to generate dihydropyrroles containing tetrasubstituted nitrogen-bearing stereocenters in 56 to 86% yield and 90:10 to 95:5 e.r.. These processes are rare examples of reactions that proceed via enantioselective migratory insertion of alkenes into Pd-N bonds, and the first where trisubstituted alkenes are used to generate tetrasubstituted stereocenters with high enantioselectivity.

U2 - 10.1039/C6SC04466B

DO - 10.1039/C6SC04466B

M3 - Article (Academic Journal)

SN - 2041-6520

VL - 8

SP - 1981

EP - 1985

JO - Chemical Science

JF - Chemical Science

IS - 3

ER -

Enantioselective Narasaka-Heck Cyclizations: Synthesis of Tetrasubstituted Nitrogen-Bearing Stereocenters

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A 13C NMR Coldprobe to Underpin Chemistry Research.

3-month Core Capability for Chemistry Research

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

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Dr Hazel A Sparkes

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