Enantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines

Ryan W. F. Kerr; Mark D. Greenhalgh; Alexandra M. Z. Slawin; Polly L.  Arnold; Andrew David Smith

doi:10.1016/j.tetasy.2016.10.012

Enantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines

Ryan W. F. Kerr
, Mark D. Greenhalgh
, Alexandra M. Z. Slawin
, Polly L. Arnold
, Andrew David Smith

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

Abstract

An enantioselective N-heterocyclic carbene catalysed formal [3+2] cycloaddition has been developed for the synthesis of oxazolindin-4-one products. The reaction of oxaziridines and α-aroyloxyaldehydes under N-heterocyclic carbene catalysis provides the formal cycloaddition products with excellent control of the diastereo- and enantioselectivity (12 examples, up to >95:5 dr, >99:1 er). A matched-mismatched effect between the enantiomer of the catalyst and oxaziridine was identified, and preliminary mechanistic studies have allowed the proposal of a model to explain these observations.

Original language	English
Pages (from-to)	125-134
Journal	Tetrahedron: Asymmetry
Volume	28
Issue number	1
Early online date	21 Nov 2016
DOIs	https://doi.org/10.1016/j.tetasy.2016.10.012
Publication status	Published - 15 Jan 2017

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10.1016/j.tetasy.2016.10.012

Kerr_2017_Enantioselective_Tetrahedron_CC
© 2017 The Authors. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).
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RS Wolfson Merit Award: Developing Catalysis Research: New Reaction Discoveries and Practical Applications
Smith, A. (PI)
The Royal Society
1/01/15 → 31/12/19
Project: Fellowship
CRITICAT CDT: Critical Resource Catalysis - CRITICAT
Smith, A. (PI), Nolan, S. (CoI) & Westwood, N. (CoI)
EPSRC
1/05/14 → 31/10/22
Project: Standard

Enantioselective NHC-catalyzed redox formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines
Smith, A. D. (Creator), Kerr, R. W. F. (Contributor), Greenhalgh, M. D. (Contributor), Slawin, A. M. Z. (Contributor) & Arnold, P. (Contributor), University of St Andrews, 10 Oct 2016
DOI: 10.17630/f9eafeea-3e54-4e50-b999-799dea11917d
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Independent and combined Lewis acid-Lewis base catalysis with N-heterocyclic carbenes and rare-earth ions
Kerr, R. W. F. (Author), Smith, A. D. (Supervisor) & Arnold, P. L. (Supervisor), 26 Jun 2019
Student thesis: Doctoral Thesis (PhD)

Cite this

@article{3fe8c26ecde5466098a97e7ff8223a23,

title = "Enantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines",

abstract = "An enantioselective N-heterocyclic carbene catalysed formal [3+2] cycloaddition has been developed for the synthesis of oxazolindin-4-one products. The reaction of oxaziridines and α-aroyloxyaldehydes under N-heterocyclic carbene catalysis provides the formal cycloaddition products with excellent control of the diastereo- and enantioselectivity (12 examples, up to >95:5 dr, >99:1 er). A matched-mismatched effect between the enantiomer of the catalyst and oxaziridine was identified, and preliminary mechanistic studies have allowed the proposal of a model to explain these observations.",

author = "Kerr, \{Ryan W. F.\} and Greenhalgh, \{Mark D.\} and Slawin, \{Alexandra M. Z.\} and Arnold, \{Polly L.\} and Smith, \{Andrew David\}",

note = "We thank the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT, grant code EP/L016419/1) (R.W.F.K.) for funding. The European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007–2013) ERC Grant Agreement No. 279850 is also acknowledged. A.D.S. thanks the Royal Society for a Wolfson Research Merit Award.",

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doi = "10.1016/j.tetasy.2016.10.012",

language = "English",

volume = "28",

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T1 - Enantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines

AU - Kerr, Ryan W. F.

AU - Greenhalgh, Mark D.

AU - Slawin, Alexandra M. Z.

AU - Arnold, Polly L.

AU - Smith, Andrew David

N1 - We thank the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT, grant code EP/L016419/1) (R.W.F.K.) for funding. The European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013) ERC Grant Agreement No. 279850 is also acknowledged. A.D.S. thanks the Royal Society for a Wolfson Research Merit Award.

PY - 2017/1/15

Y1 - 2017/1/15

N2 - An enantioselective N-heterocyclic carbene catalysed formal [3+2] cycloaddition has been developed for the synthesis of oxazolindin-4-one products. The reaction of oxaziridines and α-aroyloxyaldehydes under N-heterocyclic carbene catalysis provides the formal cycloaddition products with excellent control of the diastereo- and enantioselectivity (12 examples, up to >95:5 dr, >99:1 er). A matched-mismatched effect between the enantiomer of the catalyst and oxaziridine was identified, and preliminary mechanistic studies have allowed the proposal of a model to explain these observations.

AB - An enantioselective N-heterocyclic carbene catalysed formal [3+2] cycloaddition has been developed for the synthesis of oxazolindin-4-one products. The reaction of oxaziridines and α-aroyloxyaldehydes under N-heterocyclic carbene catalysis provides the formal cycloaddition products with excellent control of the diastereo- and enantioselectivity (12 examples, up to >95:5 dr, >99:1 er). A matched-mismatched effect between the enantiomer of the catalyst and oxaziridine was identified, and preliminary mechanistic studies have allowed the proposal of a model to explain these observations.

U2 - 10.1016/j.tetasy.2016.10.012

DO - 10.1016/j.tetasy.2016.10.012

M3 - Article

SN - 0957-4166

VL - 28

SP - 125

EP - 134

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 1

ER -

Enantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines

Abstract

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Projects

RS Wolfson Merit Award: Developing Catalysis Research: New Reaction Discoveries and Practical Applications

CRITICAT CDT: Critical Resource Catalysis - CRITICAT

Datasets

Enantioselective NHC-catalyzed redox formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines

Student theses

Independent and combined Lewis acid-Lewis base catalysis with N-heterocyclic carbenes and rare-earth ions

Cite this