Copper-Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β-and γ-Amino-alkyl)boronic Esters

Nina Ursinyova; Robin B Bedford; Timothy Gallagher

doi:10.1002/ejoc.201501492

Copper-Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β-and γ-Amino-alkyl)boronic Esters

Nina Ursinyova, Robin B Bedford, Timothy Gallagher^*

^*Corresponding author for this work

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

14 Citations (Scopus)

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Abstract

Cyclic sulfamidates undergo borylation under copper-catalyzed conditions using B₂pin₂ to give enantiomerically (and diasteromerically) defined aminoalkyl boronic esters. Extraneous iodide is essential but the intermediacy of simple alkyl iodides has been excluded; N-sulfated intermediates are key in the borylation sequence. Based on stereochemical studies and trapping experiments, the involvement of carbon-centered radicals under these copper-catalyzed conditions appears likely.

Original language	English
Pages (from-to)	673-677
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	4
Early online date	23 Dec 2015
DOIs	https://doi.org/10.1002/ejoc.201501492
Publication status	Published - 5 Feb 2016

Research Groups and Themes

BCS and TECS CDTs

Keywords

(Aminoalkyl)boronic esters
Boron
Copper
Cyclic sulfamidates
Radical reactions

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10.1002/ejoc.201501492

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© 2016 The Authors. Published by WILEY-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Final published version, 0.98 MBLicence: CC BY

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title = "Copper-Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β-and γ-Amino-alkyl)boronic Esters",

abstract = "Cyclic sulfamidates undergo borylation under copper-catalyzed conditions using B2pin2 to give enantiomerically (and diasteromerically) defined aminoalkyl boronic esters. Extraneous iodide is essential but the intermediacy of simple alkyl iodides has been excluded; N-sulfated intermediates are key in the borylation sequence. Based on stereochemical studies and trapping experiments, the involvement of carbon-centered radicals under these copper-catalyzed conditions appears likely. ",

keywords = "(Aminoalkyl)boronic esters, Boron, Copper, Cyclic sulfamidates, Radical reactions",

author = "Nina Ursinyova and Bedford, {Robin B} and Timothy Gallagher",

year = "2016",

month = feb,

day = "5",

doi = "10.1002/ejoc.201501492",

language = "English",

volume = "2016",

pages = "673--677",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

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TY - JOUR

T1 - Copper-Catalyzed Borylation of Cyclic Sulfamidates

T2 - Access to Enantiomerically Pure (β-and γ-Amino-alkyl)boronic Esters

AU - Ursinyova, Nina

AU - Bedford, Robin B

AU - Gallagher, Timothy

PY - 2016/2/5

Y1 - 2016/2/5

N2 - Cyclic sulfamidates undergo borylation under copper-catalyzed conditions using B2pin2 to give enantiomerically (and diasteromerically) defined aminoalkyl boronic esters. Extraneous iodide is essential but the intermediacy of simple alkyl iodides has been excluded; N-sulfated intermediates are key in the borylation sequence. Based on stereochemical studies and trapping experiments, the involvement of carbon-centered radicals under these copper-catalyzed conditions appears likely.

AB - Cyclic sulfamidates undergo borylation under copper-catalyzed conditions using B2pin2 to give enantiomerically (and diasteromerically) defined aminoalkyl boronic esters. Extraneous iodide is essential but the intermediacy of simple alkyl iodides has been excluded; N-sulfated intermediates are key in the borylation sequence. Based on stereochemical studies and trapping experiments, the involvement of carbon-centered radicals under these copper-catalyzed conditions appears likely.

KW - (Aminoalkyl)boronic esters

KW - Boron

KW - Copper

KW - Cyclic sulfamidates

KW - Radical reactions

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U2 - 10.1002/ejoc.201501492

DO - 10.1002/ejoc.201501492

M3 - Article (Academic Journal)

AN - SCOPUS:84952700702

SN - 1434-193X

VL - 2016

SP - 673

EP - 677

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 4

ER -

Copper-Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β-and γ-Amino-alkyl)boronic Esters

Abstract

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Copper-Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β-and γ-Amino-alkyl)boronic Esters

Abstract

Research Groups and Themes

Keywords

Access to Document

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Embargoed Document

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