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

University of Bristol

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

61 Citations (Scopus)

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
DOIs	https://doi.org/10.1002/anie.201610387
Publication status	Published - 16 Jan 2017
Externally published	Yes

Keywords

alkenes
boron
isomers
oxidation
selenium

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10.1002/anie.201610387

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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.\}",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2017",

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doi = "10.1002/anie.201610387",

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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

UR - https://www.scopus.com/pages/publications/85006741629

U2 - 10.1002/anie.201610387

DO - 10.1002/anie.201610387

M3 - Article

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

Abstract

Keywords

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