A Simple and Broadly Applicable C−N Bond Forming Dearomatization Protocol Enabled by Bifunctional Amino Reagents

Xiao-Feng Ma; Joshua Farndon; Tom Young; Natalie Fey; John Bower

doi:10.1002/anie.201708176

A Simple and Broadly Applicable C−N Bond Forming Dearomatization Protocol Enabled by Bifunctional Amino Reagents

Xiao-Feng Ma, Joshua Farndon, Tom Young, Natalie Fey, John Bower

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

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Abstract

A C-N bond forming dearomatization protocol with broad scope is outlined. Specifically, bifunctional amino-reagents are used for sequential nucleophilic and electrophilic C-N bond formations, with the latter effecting the key dearomatization step. Using this approach, γ-arylated alcohols are converted to a wide range of differentially protected spirocyclic pyrrolidines in just two or three steps.

Original language	English
Pages (from-to)	14531-14535
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	46
Early online date	11 Oct 2017
DOIs	https://doi.org/10.1002/anie.201708176
Publication status	Published - 13 Nov 2017

Structured keywords

BCS and TECS CDTs

Keywords

C−N bond
dearomatization
spirocyclic pyrrolidine

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10.1002/anie.201708176

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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

Dr Natalie Fey
- Natalie.Feybristol.acuk
- School of Chemistry - Associate Professor
- Synthesis
- Supramolecular and Mechanistic Chemistry
- Catalysis
- Computational and Theoretical Chemistry
Person: Academic , Member

Cite this

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title = "A Simple and Broadly Applicable C−N Bond Forming Dearomatization Protocol Enabled by Bifunctional Amino Reagents",

abstract = "A C-N bond forming dearomatization protocol with broad scope is outlined. Specifically, bifunctional amino-reagents are used for sequential nucleophilic and electrophilic C-N bond formations, with the latter effecting the key dearomatization step. Using this approach, γ-arylated alcohols are converted to a wide range of differentially protected spirocyclic pyrrolidines in just two or three steps.",

keywords = "C−N bond, dearomatization, spirocyclic pyrrolidine",

author = "Xiao-Feng Ma and Joshua Farndon and Tom Young and Natalie Fey and John Bower",

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language = "English",

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journal = "Angewandte Chemie - International Edition",

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AU - Ma, Xiao-Feng

AU - Farndon, Joshua

AU - Young, Tom

AU - Fey, Natalie

AU - Bower, John

PY - 2017/11/13

Y1 - 2017/11/13

N2 - A C-N bond forming dearomatization protocol with broad scope is outlined. Specifically, bifunctional amino-reagents are used for sequential nucleophilic and electrophilic C-N bond formations, with the latter effecting the key dearomatization step. Using this approach, γ-arylated alcohols are converted to a wide range of differentially protected spirocyclic pyrrolidines in just two or three steps.

AB - A C-N bond forming dearomatization protocol with broad scope is outlined. Specifically, bifunctional amino-reagents are used for sequential nucleophilic and electrophilic C-N bond formations, with the latter effecting the key dearomatization step. Using this approach, γ-arylated alcohols are converted to a wide range of differentially protected spirocyclic pyrrolidines in just two or three steps.

KW - C−N bond

KW - dearomatization

KW - spirocyclic pyrrolidine

U2 - 10.1002/anie.201708176

DO - 10.1002/anie.201708176

M3 - Article (Academic Journal)

C2 - 28925055

VL - 56

SP - 14531

EP - 14535

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 46

ER -

A Simple and Broadly Applicable C−N Bond Forming Dearomatization Protocol Enabled by Bifunctional Amino Reagents

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A 13C NMR Coldprobe to Underpin Chemistry Research.

3-month Core Capability for Chemistry Research

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Dr Natalie Fey

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