Stereodivergent Olefination of Enantioenriched Boronic Esters

Roly J. Armstrong; Cristina García-Ruiz; Eddie L. Myers; Varinder K. Aggarwal

doi:10.1002/anie.201610387

Stereodivergent Olefination of Enantioenriched Boronic Esters

Roly J. Armstrong, Cristina García-Ruiz, Eddie L. Myers, Varinder K. Aggarwal^*

^*Corresponding author for this work

School of Chemistry

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

60 Citations (Scopus)

362 Downloads (Pure)

Abstract

A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition-metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination. Chiral, nonracemic boronic esters could be coupled with complete enantiospecificity. The process enables the highly stereoselective synthesis of either the E or Z alkene from a single isomer of a vinyl coupling partner.

Original language	English
Pages (from-to)	786-790
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	3
Early online date	13 Dec 2016
DOIs	https://doi.org/10.1002/anie.201610387
Publication status	Published - 16 Jan 2017

Keywords

alkenes
boron
isomers
oxidation
selenium

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10.1002/anie.201610387

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This is the final published version of the article (version of record). It first appeared online via Wiley at https://doi.org/10.1002/anie.201610387 . Please refer to any applicable terms of use of the publisher.
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3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research
Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
Aggarwal, V. K. (Principal Investigator)
14/05/12 → 13/01/18
Project: Research

Professor Varinder K Aggarwal
- V.Aggarwalbristol.acuk
- School of Chemistry - Alfred Capper Pass Chair of Chemistry
Person: Academic

Cite this

@article{8e227bd9fe9a4da59b1894fd2f9e343c,

title = "Stereodivergent Olefination of Enantioenriched Boronic Esters",

abstract = "A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition-metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination. Chiral, nonracemic boronic esters could be coupled with complete enantiospecificity. The process enables the highly stereoselective synthesis of either the E or Z alkene from a single isomer of a vinyl coupling partner.",

keywords = "alkenes, boron, isomers, oxidation, selenium",

author = "Armstrong, {Roly J.} and Cristina Garc{\'i}a-Ruiz and Myers, {Eddie L.} and Aggarwal, {Varinder K.}",

year = "2017",

month = jan,

day = "16",

doi = "10.1002/anie.201610387",

language = "English",

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pages = "786--790",

journal = "Angewandte Chemie - International Edition",

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publisher = "Wiley-VCH Verlag",

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T1 - Stereodivergent Olefination of Enantioenriched Boronic Esters

AU - Armstrong, Roly J.

AU - García-Ruiz, Cristina

AU - Myers, Eddie L.

AU - Aggarwal, Varinder K.

PY - 2017/1/16

Y1 - 2017/1/16

N2 - A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition-metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination. Chiral, nonracemic boronic esters could be coupled with complete enantiospecificity. The process enables the highly stereoselective synthesis of either the E or Z alkene from a single isomer of a vinyl coupling partner.

AB - A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition-metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination. Chiral, nonracemic boronic esters could be coupled with complete enantiospecificity. The process enables the highly stereoselective synthesis of either the E or Z alkene from a single isomer of a vinyl coupling partner.

KW - alkenes

KW - boron

KW - isomers

KW - oxidation

KW - selenium

U2 - 10.1002/anie.201610387

DO - 10.1002/anie.201610387

M3 - Article (Academic Journal)

C2 - 27958668

AN - SCOPUS:85006741629

SN - 1433-7851

VL - 56

SP - 786

EP - 790

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 3

ER -

Stereodivergent Olefination of Enantioenriched Boronic Esters

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Keywords

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Projects

3-month Core Capability for Chemistry Research

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

Profiles

Professor Varinder K Aggarwal

Cite this