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

Research output: Contribution to journalArticle

24 Citations (Scopus)

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 languageEnglish
Pages (from-to)10530-10536
Number of pages7
JournalChemistry - A European Journal
Volume21
Issue number29
Early online date12 Jun 2015
DOIs
Publication statusPublished - 1 Jul 2015

Fingerprint

Lewis Bases
Cycloaddition
Ammonium Compounds
Catalysts

Keywords

  • asymmetric synthesis
  • heterocycles
  • Lewis base
  • organocatalysis
  • oxaziridines

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Smith, S. R., Fallan, C., Taylor, J. E., McLennan, R., Daniels, D. S. B., Morrill, L. C., ... Smith, A. D. (2015). Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines. Chemistry - A European Journal, 21(29), 10530-10536. https://doi.org/10.1002/chem.201501271

Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines. / Smith, Siobhan R.; Fallan, Charlene; Taylor, James E.; McLennan, Ross; Daniels, David S.B.; Morrill, Louis C.; Slawin, Alexandra M.Z.; Smith, Andrew D.

In: Chemistry - A European Journal, Vol. 21, No. 29, 01.07.2015, p. 10530-10536.

Research output: Contribution to journalArticle

Smith, SR, Fallan, C, Taylor, JE, McLennan, R, Daniels, DSB, Morrill, LC, Slawin, AMZ & Smith, AD 2015, 'Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines', Chemistry - A European Journal, vol. 21, no. 29, pp. 10530-10536. https://doi.org/10.1002/chem.201501271
Smith, Siobhan R. ; Fallan, Charlene ; Taylor, James E. ; McLennan, Ross ; Daniels, David S.B. ; Morrill, Louis C. ; Slawin, Alexandra M.Z. ; Smith, Andrew D. / Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines. In: Chemistry - A European Journal. 2015 ; Vol. 21, No. 29. pp. 10530-10536.
@article{6eda49d4e91d45f7a2b37399e991c219,
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.}",
year = "2015",
month = "7",
day = "1",
doi = "10.1002/chem.201501271",
language = "English",
volume = "21",
pages = "10530--10536",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-Blackwell",
number = "29",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=84934299973&partnerID=8YFLogxK

U2 - 10.1002/chem.201501271

DO - 10.1002/chem.201501271

M3 - Article

VL - 21

SP - 10530

EP - 10536

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 29

ER -