A consecutive process for C–C and C–N bond formation with high enantio-and diastereocontrol: direct reductive amination of chiral ketones using hydrogenation catalysts

Sophie H. Gilbert; Virginie Viseur; Matthew L. Clarke

doi:10.1039/c9cc00923j

A consecutive process for C–C and C–N bond formation with high enantio-and diastereocontrol: direct reductive amination of chiral ketones using hydrogenation catalysts

Sophie H. Gilbert, Virginie Viseur, Matthew L. Clarke

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

Abstract

High diastereoselectivity was observed in the Rh-catalysed reductive amination of 3-arylcyclohexanones to form tertiary amines. This was incorporated into a one-pot enantioselective conjugate addition and diastereoselective reductive amination, including an example of assisted tandem catalysis.

Original language	English
Pages (from-to)	6409-6412
Number of pages	4
Journal	Chemical Communications
Volume	55
Issue number	45
Early online date	10 May 2019
DOIs	https://doi.org/10.1039/c9cc00923j
Publication status	Published - 7 Jun 2019

Keywords

Asymmetric hydrogenation
Reductive amination
Homogeneous catalysis

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10.1039/c9cc00923j

Diastereoredamacceptedversionpdf
Copyright © 2019 The Author(s). This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1039/C9CC00923J
Accepted author manuscript, 504 KB

CRITICAT CDT: Critical Resource Catalysis - CRITICAT
Smith, A. D. (PI), Nolan, S. P. (CoI) & Westwood, N. J. (CoI)
EPSRC
1/05/14 → 31/10/22
Project: Standard

A consecutive process for C-C and C-N bond formation with high enantio-and diastereo-control: Direct Reductive Amination of chiral ketones using hydrogenation catalysts (dataset)
Gilbert, S. H. (Creator), Viseur, V. (Contributor) & Clarke, M. L. (Supervisor), University of St Andrews, 20 May 2019
DOI: 10.17630/9835792a-fd68-4622-b273-3868b664b500
Dataset

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Cite this

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title = "A consecutive process for C–C and C–N bond formation with high enantio-and diastereocontrol: direct reductive amination of chiral ketones using hydrogenation catalysts",

abstract = "High diastereoselectivity was observed in the Rh-catalysed reductive amination of 3-arylcyclohexanones to form tertiary amines. This was incorporated into a one-pot enantioselective conjugate addition and diastereoselective reductive amination, including an example of assisted tandem catalysis.",

keywords = "Asymmetric hydrogenation, Reductive amination, Homogeneous catalysis",

author = "Gilbert, {Sophie H.} and Virginie Viseur and Clarke, {Matthew L.}",

note = "Authors thank the University of St Andrews, and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT) for financial support [PhD studentship to SG; Grant code: EP/L016419/1]. ",

year = "2019",

month = jun,

day = "7",

doi = "10.1039/c9cc00923j",

language = "English",

volume = "55",

pages = "6409--6412",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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}

A consecutive process for C–C and C–N bond formation with high enantio-and diastereocontrol: direct reductive amination of chiral ketones using hydrogenation catalysts. / Gilbert, Sophie H.; Viseur, Virginie; Clarke, Matthew L.
In: Chemical Communications, Vol. 55, No. 45, 07.06.2019, p. 6409-6412.

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

TY - JOUR

T1 - A consecutive process for C–C and C–N bond formation with high enantio-and diastereocontrol

T2 - direct reductive amination of chiral ketones using hydrogenation catalysts

AU - Gilbert, Sophie H.

AU - Viseur, Virginie

AU - Clarke, Matthew L.

N1 - Authors thank the University of St Andrews, and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT) for financial support [PhD studentship to SG; Grant code: EP/L016419/1].

PY - 2019/6/7

Y1 - 2019/6/7

N2 - High diastereoselectivity was observed in the Rh-catalysed reductive amination of 3-arylcyclohexanones to form tertiary amines. This was incorporated into a one-pot enantioselective conjugate addition and diastereoselective reductive amination, including an example of assisted tandem catalysis.

AB - High diastereoselectivity was observed in the Rh-catalysed reductive amination of 3-arylcyclohexanones to form tertiary amines. This was incorporated into a one-pot enantioselective conjugate addition and diastereoselective reductive amination, including an example of assisted tandem catalysis.

KW - Asymmetric hydrogenation

KW - Reductive amination

KW - Homogeneous catalysis

U2 - 10.1039/c9cc00923j

DO - 10.1039/c9cc00923j

M3 - Article

SN - 1359-7345

VL - 55

SP - 6409

EP - 6412

JO - Chemical Communications

JF - Chemical Communications

IS - 45

ER -

A consecutive process for C–C and C–N bond formation with high enantio-and diastereocontrol: direct reductive amination of chiral ketones using hydrogenation catalysts

Abstract

Keywords

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Projects

CRITICAT CDT: Critical Resource Catalysis - CRITICAT

Datasets

A consecutive process for C-C and C-N bond formation with high enantio-and diastereo-control: Direct Reductive Amination of chiral ketones using hydrogenation catalysts (dataset)

Cite this