Enantioselective Rhodium(III)-Catalyzed Markovnikov Hydroboration of Unactivated Terminal Alkenes

James R Smith; Beatrice S L Collins; Matthew J Hesse; Mark A Graham; Eddie L Myers; Varinder K Aggarwal

doi:10.1021/jacs.7b05149

Enantioselective Rhodium(III)-Catalyzed Markovnikov Hydroboration of Unactivated Terminal Alkenes

James R Smith, Beatrice S L Collins, Matthew J Hesse, Mark A Graham, Eddie L Myers, Varinder K Aggarwal

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

112 Citations (Scopus)

450 Downloads (Pure)

Abstract

We report the first enantioselective Rh-catalyzed Markovnikov hydroboration of unactivated terminal alkenes. Using a novel sp(2)-sp(3) hybridized diboron reagent and water as a proton source, a broad range of alkenes undergo hydroboration to provide secondary boronic esters with high regio- and enantiocontrol.

Original language	English
Pages (from-to)	9148-9151
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	27
DOIs	https://doi.org/10.1021/jacs.7b05149
Publication status	Published - 30 Jun 2017

Research Groups and Themes

BCS and TECS CDTs
Organic & Biological

Keywords

Journal Article

Access to Document

10.1021/jacs.7b05149

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This is the final published version of the article (version of record). It first appeared online via ACS at http://pubs.acs.org/doi/10.1021/jacs.7b05149. Please refer to any applicable terms of use of the publisher.
Final published version, 1.21 MBLicence: CC BY

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FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds
Aggarwal, V. K. (Principal Investigator)
1/10/15 → 31/03/21
Project: Research
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
Dr Beatrice Collins
- bs.lefanucollinsbristol.acuk
- School of Chemistry - Royal Society Research Fellow/Proleptic Lectureship
Person: Academic

Cite this

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title = "Enantioselective Rhodium(III)-Catalyzed Markovnikov Hydroboration of Unactivated Terminal Alkenes",

abstract = "We report the first enantioselective Rh-catalyzed Markovnikov hydroboration of unactivated terminal alkenes. Using a novel sp(2)-sp(3) hybridized diboron reagent and water as a proton source, a broad range of alkenes undergo hydroboration to provide secondary boronic esters with high regio- and enantiocontrol.",

keywords = "Journal Article",

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year = "2017",

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doi = "10.1021/jacs.7b05149",

language = "English",

volume = "139",

pages = "9148--9151",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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T1 - Enantioselective Rhodium(III)-Catalyzed Markovnikov Hydroboration of Unactivated Terminal Alkenes

AU - Smith, James R

AU - Collins, Beatrice S L

AU - Hesse, Matthew J

AU - Graham, Mark A

AU - Myers, Eddie L

AU - Aggarwal, Varinder K

PY - 2017/6/30

Y1 - 2017/6/30

N2 - We report the first enantioselective Rh-catalyzed Markovnikov hydroboration of unactivated terminal alkenes. Using a novel sp(2)-sp(3) hybridized diboron reagent and water as a proton source, a broad range of alkenes undergo hydroboration to provide secondary boronic esters with high regio- and enantiocontrol.

AB - We report the first enantioselective Rh-catalyzed Markovnikov hydroboration of unactivated terminal alkenes. Using a novel sp(2)-sp(3) hybridized diboron reagent and water as a proton source, a broad range of alkenes undergo hydroboration to provide secondary boronic esters with high regio- and enantiocontrol.

KW - Journal Article

U2 - 10.1021/jacs.7b05149

DO - 10.1021/jacs.7b05149

M3 - Article (Academic Journal)

C2 - 28665124

SN - 0002-7863

VL - 139

SP - 9148

EP - 9151

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 27

ER -

Enantioselective Rhodium(III)-Catalyzed Markovnikov Hydroboration of Unactivated Terminal Alkenes

Abstract

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Projects

FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds

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

Dr Beatrice Collins

Cite this