Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines

Siobhan R. Smith; Charlene Fallan; James E. Taylor; Ross McLennan; David S.B. Daniels; Louis C. Morrill; Alexandra M.Z. Slawin; Andrew D. Smith

doi:10.1002/chem.201501271

Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines

Siobhan R. Smith, Charlene Fallan, James E. Taylor, Ross McLennan, David S.B. Daniels, Louis C. Morrill, Alexandra M.Z. Slawin, Andrew D. Smith

Department of Chemistry

University of St Andrews

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

41 Citations (SciVal)

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 d.r., 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
Number of pages	7
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 - 1 Jul 2015

Keywords

asymmetric synthesis
heterocycles
Lewis base
organocatalysis
oxaziridines

ASJC Scopus subject areas

General Chemistry

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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 d.r., yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks.",

keywords = "asymmetric synthesis, heterocycles, Lewis base, organocatalysis, oxaziridines",

author = "Smith, \{Siobhan R.\} and Charlene Fallan and Taylor, \{James E.\} and Ross McLennan and Daniels, \{David S.B.\} and Morrill, \{Louis C.\} and Slawin, \{Alexandra M.Z.\} and Smith, \{Andrew D.\}",

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T1 - Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines

AU - Smith, Siobhan R.

AU - Fallan, Charlene

AU - Taylor, James E.

AU - McLennan, Ross

AU - Daniels, David S.B.

AU - Morrill, Louis C.

AU - Slawin, Alexandra M.Z.

AU - Smith, Andrew D.

PY - 2015/7/1

Y1 - 2015/7/1

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 d.r., 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 d.r., yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks.

KW - asymmetric synthesis

KW - heterocycles

KW - Lewis base

KW - organocatalysis

KW - oxaziridines

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DO - 10.1002/chem.201501271

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Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines

Abstract

Keywords

ASJC Scopus subject areas

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