An alternative synthesis of cycloalkyl-substituted CPA catalysts and application in asymmetric protonation reactions

Liam McLean; Allan J. B. Watson

doi:10.1002/ejoc.202100980

An alternative synthesis of cycloalkyl-substituted CPA catalysts and application in asymmetric protonation reactions

Liam McLean, Allan J. B. Watson^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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Abstract

An alternative synthesis of cycloalkyl-substituted CPA catalysts is reported. A Negishi coupling offers improved yields and purity of the necessary 1,3,5-tri(cycloalkyl)benzenes. Limitations in the use of commercial organozinc reagents have been identified and a robust procedure for the preparation of these reagents is detailed. Similarly, a robust procedure for the key Kumada coupling is also provided. The route is demonstrated by preparation of three different tri(cycloalkyl)aryl-substituted CPAs and the utility of these catalysts in asymmetric protonation reactions is shown.

Original language	English
Pages (from-to)	4943-4945
Number of pages	4
Journal	European Journal of Organic Chemistry
Issue number	35
DOIs	https://doi.org/10.1002/ejoc.202100980
Publication status	Published - 15 Sept 2021

Keywords

Asymmetric protonation
Brønsted acid
Catalysis
Cross-coupling
Enantioselectivity

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10.1002/ejoc.202100980Licence: CC BY

McLean_2021_EJoC_alternative-synthesis_CC
Copyright © 2021 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH. 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, 2.84 MBLicence: CC BY

Accessing Pharmacophoric Space: Accessing Pharmacophoric Space Via Asymmetric Protonation
Watson, A. J. B. (PI)
EPSRC
1/10/19 → 30/09/22
Project: Standard

Dataset underpinning "An alternative synthesis of cycloalkyl-substituted CPA catalysts and application in asymmetric protonation reactions"
Watson, A. J. B. (Creator), University of St Andrews, 16 Sept 2021
DOI: 10.17630/2d4dea0c-af38-4102-8dc9-684f5e6ab525
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File

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keywords = "Asymmetric protonation, Br{\o}nsted acid, Catalysis, Cross-coupling, Enantioselectivity",

author = "Liam McLean and Watson, {Allan J. B.}",

note = "LAM thanks the EPSRC (grant number EP/S027165/1) for postdoctoral funding.",

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doi = "10.1002/ejoc.202100980",

language = "English",

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T1 - An alternative synthesis of cycloalkyl-substituted CPA catalysts and application in asymmetric protonation reactions

AU - McLean, Liam

AU - Watson, Allan J. B.

N1 - LAM thanks the EPSRC (grant number EP/S027165/1) for postdoctoral funding.

PY - 2021/9/15

Y1 - 2021/9/15

N2 - An alternative synthesis of cycloalkyl-substituted CPA catalysts is reported. A Negishi coupling offers improved yields and purity of the necessary 1,3,5-tri(cycloalkyl)benzenes. Limitations in the use of commercial organozinc reagents have been identified and a robust procedure for the preparation of these reagents is detailed. Similarly, a robust procedure for the key Kumada coupling is also provided. The route is demonstrated by preparation of three different tri(cycloalkyl)aryl-substituted CPAs and the utility of these catalysts in asymmetric protonation reactions is shown.

AB - An alternative synthesis of cycloalkyl-substituted CPA catalysts is reported. A Negishi coupling offers improved yields and purity of the necessary 1,3,5-tri(cycloalkyl)benzenes. Limitations in the use of commercial organozinc reagents have been identified and a robust procedure for the preparation of these reagents is detailed. Similarly, a robust procedure for the key Kumada coupling is also provided. The route is demonstrated by preparation of three different tri(cycloalkyl)aryl-substituted CPAs and the utility of these catalysts in asymmetric protonation reactions is shown.

KW - Asymmetric protonation

KW - Brønsted acid

KW - Catalysis

KW - Cross-coupling

KW - Enantioselectivity

U2 - 10.1002/ejoc.202100980

DO - 10.1002/ejoc.202100980

M3 - Article

SN - 1434-193X

SP - 4943

EP - 4945

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 35

ER -

An alternative synthesis of cycloalkyl-substituted CPA catalysts and application in asymmetric protonation reactions

Abstract

Keywords

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Projects

Accessing Pharmacophoric Space: Accessing Pharmacophoric Space Via Asymmetric Protonation

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Dataset underpinning "An alternative synthesis of cycloalkyl-substituted CPA catalysts and application in asymmetric protonation reactions"

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