Enantioselective Stereodivergent Nucleophile-Dependent Isothiourea-Catalysed Domino Reactions

Anastassia Matviitsuk; James E. Taylor; David B. Cordes; Alexandra M.Z. Slawin; Andrew D. Smith

doi:10.1002/chem.201603318

Enantioselective Stereodivergent Nucleophile-Dependent Isothiourea-Catalysed Domino Reactions

Anastassia Matviitsuk, James E. Taylor, David B. Cordes, Alexandra M.Z. Slawin, Andrew D. Smith

Department of Chemistry

University of St Andrews

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

31 Citations (SciVal)

Abstract

α,β-Unsaturated acyl ammoniums generated from the reaction of α,β-unsaturated 2,4,6-trichlorophenol (TCP) esters bearing a pendent enone with an isothiourea organocatalyst are versatile intermediates in a range of enantioselective nucleophile-dependent domino processes to form complex products of diverse topology with excellent stereoselectivity. Use of either 1,3-dicarbonyls, acyl benzothiazoles, or acyl benzimidazoles as nucleophiles allows three distinct, diastereodivergent domino reaction pathways to be accessed to form various fused polycyclic cores containing multiple contiguous stereocentres.

Original language	English
Pages (from-to)	17748-17757
Number of pages	10
Journal	Chemistry - A European Journal
Volume	22
Issue number	49
Early online date	11 Oct 2016
DOIs	https://doi.org/10.1002/chem.201603318
Publication status	Published - 5 Dec 2016

Keywords

domino reactions
enantioselective synthesis
Lewis base
organocatalysis
α,β-unsaturated acyl ammonium

ASJC Scopus subject areas

General Chemistry

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10.1002/chem.201603318Licence: CC BY

Cite this

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title = "Enantioselective Stereodivergent Nucleophile-Dependent Isothiourea-Catalysed Domino Reactions",

abstract = "α,β-Unsaturated acyl ammoniums generated from the reaction of α,β-unsaturated 2,4,6-trichlorophenol (TCP) esters bearing a pendent enone with an isothiourea organocatalyst are versatile intermediates in a range of enantioselective nucleophile-dependent domino processes to form complex products of diverse topology with excellent stereoselectivity. Use of either 1,3-dicarbonyls, acyl benzothiazoles, or acyl benzimidazoles as nucleophiles allows three distinct, diastereodivergent domino reaction pathways to be accessed to form various fused polycyclic cores containing multiple contiguous stereocentres.",

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AU - Matviitsuk, Anastassia

AU - Taylor, James E.

AU - Cordes, David B.

AU - Slawin, Alexandra M.Z.

AU - Smith, Andrew D.

PY - 2016/12/5

Y1 - 2016/12/5

N2 - α,β-Unsaturated acyl ammoniums generated from the reaction of α,β-unsaturated 2,4,6-trichlorophenol (TCP) esters bearing a pendent enone with an isothiourea organocatalyst are versatile intermediates in a range of enantioselective nucleophile-dependent domino processes to form complex products of diverse topology with excellent stereoselectivity. Use of either 1,3-dicarbonyls, acyl benzothiazoles, or acyl benzimidazoles as nucleophiles allows three distinct, diastereodivergent domino reaction pathways to be accessed to form various fused polycyclic cores containing multiple contiguous stereocentres.

AB - α,β-Unsaturated acyl ammoniums generated from the reaction of α,β-unsaturated 2,4,6-trichlorophenol (TCP) esters bearing a pendent enone with an isothiourea organocatalyst are versatile intermediates in a range of enantioselective nucleophile-dependent domino processes to form complex products of diverse topology with excellent stereoselectivity. Use of either 1,3-dicarbonyls, acyl benzothiazoles, or acyl benzimidazoles as nucleophiles allows three distinct, diastereodivergent domino reaction pathways to be accessed to form various fused polycyclic cores containing multiple contiguous stereocentres.

KW - domino reactions

KW - enantioselective synthesis

KW - Lewis base

KW - organocatalysis

KW - α,β-unsaturated acyl ammonium

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DO - 10.1002/chem.201603318

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Enantioselective Stereodivergent Nucleophile-Dependent Isothiourea-Catalysed Domino Reactions

Abstract

Keywords

ASJC Scopus subject areas

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