Phospholane-phosphite ligands for Rh catalyzed enantioselective conjugate addition: unusually reactive catalysts for challenging couplings

Sophie H. Gilbert; José A. Fuentes; David B. Cordes; Alexandra M. Z. Slawin; Matthew L. Clarke

doi:10.1002/ejoc.202000336

Phospholane-phosphite ligands for Rh catalyzed enantioselective conjugate addition: unusually reactive catalysts for challenging couplings

Sophie H. Gilbert
, José A. Fuentes
, David B. Cordes
, Alexandra M. Z. Slawin
, Matthew L. Clarke

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

Abstract

The use of Rh catalysts derived from a phospholane-phosphite ligand were found to be more productive than the classic rhodium/BINAP system in enantioselective conjugate additions. These catalysts enable the use of lower amounts of aryl boronic acid in an asymmetric arylation reaction that required an impractical excess of nucleophile. This catalyst was also found to enable the coupling of a poorly reactive Michael acceptor, N-CBz-2-3-dehydro-4-piperidone, or the coupling of poorly reactive 2-furyl boronic acids at ambient or near temperatures.

Original language	English
Pages (from-to)	3071-3076
Journal	European Journal of Organic Chemistry
Volume	2020
Issue number	20
Early online date	8 May 2020
DOIs	https://doi.org/10.1002/ejoc.202000336
Publication status	Published - 25 May 2020

Keywords

Asymmetric arylation
Michael addition
Aryl boronic acids
Phospholane ligands
Asymmetric catalysis

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10.1002/ejoc.202000336Licence: CC BY

Gilbert_2020_EJOC_Rh_CC
Copyright © 2020 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. 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, 0.98 MBLicence: CC BY

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Enantioselective Carbonylations: New Insights New Catalysts and New Processes using Enantioselective Carbonylations
Clarke, M. (PI) & Buehl, M. (CoI)
EPSRC
1/09/14 → 30/11/17
Project: Standard
CRITICAT CDT: Critical Resource Catalysis - CRITICAT
Smith, A. (PI), Nolan, S. (CoI) & Westwood, N. (CoI)
EPSRC
1/05/14 → 31/10/22
Project: Standard

Phospholane-phosphite ligands for Rh catalysed enantioselective conjugate addition: unusually reactive catalysts for challenging couplings (dataset)
Gilbert, S. H. (Creator), Fuentes García, J. A. (Contributor), Cordes, D. B. (Contributor), Slawin, A. M. Z. (Contributor) & Clarke, M. (Supervisor), University of St Andrews, 15 Feb 2020
DOI: 10.17630/bf27a028-7eb7-472b-8891-c3558bbcae8a
Dataset

File
CCDC 1976224: Experimental Crystal Structure Determination
Gilbert, S. H. (Contributor), Fuentes, J. A. (Contributor), Cordes, D. B. (Contributor), Slawin, A. M. Z. (Contributor) & Clarke, M. L. (Contributor), The Cambridge Structural Database, 8 Jan 2020
DOI: 10.5517/ccdc.csd.cc24bf53, https://doi.org/10.5517%2Fccdc.csd.cc24bf53
Dataset

Cite this

@article{a4196d8ddd1a4765885f895488dc5ad2,

title = "Phospholane-phosphite ligands for Rh catalyzed enantioselective conjugate addition: unusually reactive catalysts for challenging couplings",

abstract = "The use of Rh catalysts derived from a phospholane-phosphite ligand were found to be more productive than the classic rhodium/BINAP system in enantioselective conjugate additions. These catalysts enable the use of lower amounts of aryl boronic acid in an asymmetric arylation reaction that required an impractical excess of nucleophile. This catalyst was also found to enable the coupling of a poorly reactive Michael acceptor, N-CBz-2-3-dehydro-4-piperidone, or the coupling of poorly reactive 2-furyl boronic acids at ambient or near temperatures.",

keywords = "Asymmetric arylation, Michael addition, Aryl boronic acids, Phospholane ligands, Asymmetric catalysis",

author = "Gilbert, \{Sophie H.\} and Fuentes, \{Jos{\'e} A.\} and Cordes, \{David B.\} and Slawin, \{Alexandra M. Z.\} and Clarke, \{Matthew L.\}",

note = "We would like to thank the University of St Andrews, and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT) for financial support [Ph.D. studentship to SG; Grant code: EP/L016419/1], and the EPSRC for funding of JAF (EP/M003868/1).",

year = "2020",

month = may,

day = "25",

doi = "10.1002/ejoc.202000336",

language = "English",

volume = "2020",

pages = "3071--3076",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH, Weinheim",

number = "20",

}

TY - JOUR

T1 - Phospholane-phosphite ligands for Rh catalyzed enantioselective conjugate addition

T2 - unusually reactive catalysts for challenging couplings

AU - Gilbert, Sophie H.

AU - Fuentes, José A.

AU - Cordes, David B.

AU - Slawin, Alexandra M. Z.

AU - Clarke, Matthew L.

N1 - We would like to thank the University of St Andrews, and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT) for financial support [Ph.D. studentship to SG; Grant code: EP/L016419/1], and the EPSRC for funding of JAF (EP/M003868/1).

PY - 2020/5/25

Y1 - 2020/5/25

N2 - The use of Rh catalysts derived from a phospholane-phosphite ligand were found to be more productive than the classic rhodium/BINAP system in enantioselective conjugate additions. These catalysts enable the use of lower amounts of aryl boronic acid in an asymmetric arylation reaction that required an impractical excess of nucleophile. This catalyst was also found to enable the coupling of a poorly reactive Michael acceptor, N-CBz-2-3-dehydro-4-piperidone, or the coupling of poorly reactive 2-furyl boronic acids at ambient or near temperatures.

AB - The use of Rh catalysts derived from a phospholane-phosphite ligand were found to be more productive than the classic rhodium/BINAP system in enantioselective conjugate additions. These catalysts enable the use of lower amounts of aryl boronic acid in an asymmetric arylation reaction that required an impractical excess of nucleophile. This catalyst was also found to enable the coupling of a poorly reactive Michael acceptor, N-CBz-2-3-dehydro-4-piperidone, or the coupling of poorly reactive 2-furyl boronic acids at ambient or near temperatures.

KW - Asymmetric arylation

KW - Michael addition

KW - Aryl boronic acids

KW - Phospholane ligands

KW - Asymmetric catalysis

U2 - 10.1002/ejoc.202000336

DO - 10.1002/ejoc.202000336

M3 - Article

SN - 1434-193X

VL - 2020

SP - 3071

EP - 3076

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 20

ER -

Phospholane-phosphite ligands for Rh catalyzed enantioselective conjugate addition: unusually reactive catalysts for challenging couplings

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Projects

Enantioselective Carbonylations: New Insights New Catalysts and New Processes using Enantioselective Carbonylations

CRITICAT CDT: Critical Resource Catalysis - CRITICAT

Datasets

Phospholane-phosphite ligands for Rh catalysed enantioselective conjugate addition: unusually reactive catalysts for challenging couplings (dataset)

CCDC 1976224: Experimental Crystal Structure Determination

Cite this