Stereospecific conversion of alcohols into pinacol boronic esters using lithiation-borylation methodology with pinacolborane

Stefan Roesner; Christopher A. Brown; Maziar Mohiti; Alexander P. Pulis; Ramesh Rasappan; Daniel J. Blair; Stephanie Essafi; Daniele Leonori; Varinder K. Aggarwal

doi:10.1039/c4cc00993b

Stereospecific conversion of alcohols into pinacol boronic esters using lithiation-borylation methodology with pinacolborane

Stefan Roesner, Christopher A. Brown, Maziar Mohiti, Alexander P. Pulis, Ramesh Rasappan, Daniel J. Blair, Stephanie Essafi, Daniele Leonori, Varinder K. Aggarwal^*

^*Corresponding author for this work

School of Chemistry

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

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Abstract

The synthesis of primary and secondary pinacol boronic esters via lithiation-borylation of carbamates and benzoates with pinacolborane is described. This new protocol enables the highly selective synthesis of enantioenriched and geometrically defined boronic esters that cannot otherwise be accessed by alternative methodologies.

Original language	English
Pages (from-to)	4053-4055
Number of pages	3
Journal	Chemical Communications
Volume	50
Issue number	31
Early online date	26 Feb 2014
DOIs	https://doi.org/10.1039/c4cc00993b
Publication status	Published - 2014

Keywords

ASYMMETRIC HYDROBORATION
ELECTROPHILIC SUBSTITUTION
CATALYZED BORYLATION
ALKYLBORONIC ESTERS
SECONDARY ALCOHOLS
COUPLING REACTIONS
ALKYL-HALIDES
DERIVATIVES
ALLYLATION
GENERATION

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10.1039/c4cc00993b

Roesner ChemCommun 2014Accepted author manuscript, 684 KB

http://pubs.rsc.org/en/Content/ArticleLanding/2014/CC/c4cc00993b#!divAbstract

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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

Cite this

@article{cb81edf09ab34070945922c26cc349a9,

title = "Stereospecific conversion of alcohols into pinacol boronic esters using lithiation-borylation methodology with pinacolborane",

abstract = "The synthesis of primary and secondary pinacol boronic esters via lithiation-borylation of carbamates and benzoates with pinacolborane is described. This new protocol enables the highly selective synthesis of enantioenriched and geometrically defined boronic esters that cannot otherwise be accessed by alternative methodologies.",

keywords = "ASYMMETRIC HYDROBORATION, ELECTROPHILIC SUBSTITUTION, CATALYZED BORYLATION, ALKYLBORONIC ESTERS, SECONDARY ALCOHOLS, COUPLING REACTIONS, ALKYL-HALIDES, DERIVATIVES, ALLYLATION, GENERATION",

author = "Stefan Roesner and Brown, {Christopher A.} and Maziar Mohiti and Pulis, {Alexander P.} and Ramesh Rasappan and Blair, {Daniel J.} and Stephanie Essafi and Daniele Leonori and Aggarwal, {Varinder K.}",

year = "2014",

doi = "10.1039/c4cc00993b",

language = "English",

volume = "50",

pages = "4053--4055",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "31",

}

TY - JOUR

T1 - Stereospecific conversion of alcohols into pinacol boronic esters using lithiation-borylation methodology with pinacolborane

AU - Roesner, Stefan

AU - Brown, Christopher A.

AU - Mohiti, Maziar

AU - Pulis, Alexander P.

AU - Rasappan, Ramesh

AU - Blair, Daniel J.

AU - Essafi, Stephanie

AU - Leonori, Daniele

AU - Aggarwal, Varinder K.

PY - 2014

Y1 - 2014

N2 - The synthesis of primary and secondary pinacol boronic esters via lithiation-borylation of carbamates and benzoates with pinacolborane is described. This new protocol enables the highly selective synthesis of enantioenriched and geometrically defined boronic esters that cannot otherwise be accessed by alternative methodologies.

AB - The synthesis of primary and secondary pinacol boronic esters via lithiation-borylation of carbamates and benzoates with pinacolborane is described. This new protocol enables the highly selective synthesis of enantioenriched and geometrically defined boronic esters that cannot otherwise be accessed by alternative methodologies.

KW - ASYMMETRIC HYDROBORATION

KW - ELECTROPHILIC SUBSTITUTION

KW - CATALYZED BORYLATION

KW - ALKYLBORONIC ESTERS

KW - SECONDARY ALCOHOLS

KW - COUPLING REACTIONS

KW - ALKYL-HALIDES

KW - DERIVATIVES

KW - ALLYLATION

KW - GENERATION

U2 - 10.1039/c4cc00993b

DO - 10.1039/c4cc00993b

M3 - Article (Academic Journal)

C2 - 24623123

SN - 1359-7345

VL - 50

SP - 4053

EP - 4055

JO - Chemical Communications

JF - Chemical Communications

IS - 31

ER -

Stereospecific conversion of alcohols into pinacol boronic esters using lithiation-borylation methodology with pinacolborane

Abstract

Keywords

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

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