Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines

Siobhan Rose Smith; Charlene Fallan; James Edward Taylor; Ross Sinclair McLennan; David Sydney Bernard Daniels; Louis Christian Morrill; Alexandra Martha Zoya Slawin; Andrew David Smith

doi:10.1002/chem.201501271

Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines

Siobhan Rose Smith
, Charlene Fallan
, James Edward Taylor
, Ross Sinclair McLennan
, David Sydney Bernard Daniels
, Louis Christian Morrill
, Alexandra Martha Zoya Slawin
, Andrew David Smith

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

Abstract

A highly enantioselective Lewis base-catalysed formal [3+2] cycloaddition of ammonium enolates and oxaziridines to give stereodefined oxazolidin-4-ones in high yield is described. Employing an enantioenriched oxaziridine in this process leads to a matched/mis-matched effect with the isothiourea catalyst and allowed the synthesis of either syn- or anti-stereodefined oxazolidin-4-ones in high dr, yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks.

Original language	English
Pages (from-to)	10530–10536
Journal	Chemistry - A European Journal
Volume	21
Issue number	29
Early online date	12 Jun 2015
DOIs	https://doi.org/10.1002/chem.201501271
Publication status	Published - 13 Jul 2015

Keywords

Organocatalysis
Nitrogen heterocycles
Oxygen heterocycles
Asymmetric synthesis

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Smith_2015_CHEMEUJ_Asymmetric_CC
© 2015 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.
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@article{bc5a8d9a5cdb49b7b00515f0fe83f974,

title = "Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines",

abstract = "A highly enantioselective Lewis base-catalysed formal [3+2] cycloaddition of ammonium enolates and oxaziridines to give stereodefined oxazolidin-4-ones in high yield is described. Employing an enantioenriched oxaziridine in this process leads to a matched/mis-matched effect with the isothiourea catalyst and allowed the synthesis of either syn- or anti-stereodefined oxazolidin-4-ones in high dr, yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks.",

keywords = "Organocatalysis, Nitrogen heterocycles, Oxygen heterocycles, Asymmetric synthesis",

author = "Smith, \{Siobhan Rose\} and Charlene Fallan and Taylor, \{James Edward\} and McLennan, \{Ross Sinclair\} and Daniels, \{David Sydney Bernard\} and Morrill, \{Louis Christian\} and Slawin, \{Alexandra Martha Zoya\} and Smith, \{Andrew David\}",

note = "The authors thank the Royal Society for a University Research Fellowship (A.D.S.) and the European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007—2013), ERC Grant Agreement No. 279850 (C.F. and J.E.T.), GSK (CASE award to S.R.S.) and EPSRC grant No. EP/J018139/1 (D.S.B.D.) for funding. ",

year = "2015",

month = jul,

day = "13",

doi = "10.1002/chem.201501271",

language = "English",

volume = "21",

pages = "10530–10536",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley \& Sons, Ltd",

number = "29",

}

TY - JOUR

T1 - Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines

AU - Smith, Siobhan Rose

AU - Fallan, Charlene

AU - Taylor, James Edward

AU - McLennan, Ross Sinclair

AU - Daniels, David Sydney Bernard

AU - Morrill, Louis Christian

AU - Slawin, Alexandra Martha Zoya

AU - Smith, Andrew David

N1 - The authors thank the Royal Society for a University Research Fellowship (A.D.S.) and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007—2013), ERC Grant Agreement No. 279850 (C.F. and J.E.T.), GSK (CASE award to S.R.S.) and EPSRC grant No. EP/J018139/1 (D.S.B.D.) for funding.

PY - 2015/7/13

Y1 - 2015/7/13

N2 - A highly enantioselective Lewis base-catalysed formal [3+2] cycloaddition of ammonium enolates and oxaziridines to give stereodefined oxazolidin-4-ones in high yield is described. Employing an enantioenriched oxaziridine in this process leads to a matched/mis-matched effect with the isothiourea catalyst and allowed the synthesis of either syn- or anti-stereodefined oxazolidin-4-ones in high dr, yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks.

AB - A highly enantioselective Lewis base-catalysed formal [3+2] cycloaddition of ammonium enolates and oxaziridines to give stereodefined oxazolidin-4-ones in high yield is described. Employing an enantioenriched oxaziridine in this process leads to a matched/mis-matched effect with the isothiourea catalyst and allowed the synthesis of either syn- or anti-stereodefined oxazolidin-4-ones in high dr, yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks.

KW - Organocatalysis

KW - Nitrogen heterocycles

KW - Oxygen heterocycles

KW - Asymmetric synthesis

UR - http://onlinelibrary.wiley.com/doi/10.1002/chem.201501271/suppinfo

U2 - 10.1002/chem.201501271

DO - 10.1002/chem.201501271

M3 - Article

SN - 0947-6539

VL - 21

SP - 10530

EP - 10536

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 29

ER -

Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines

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Keywords

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