Anhydrides as α,β-unsaturated acyl ammonium precursors: isothiourea-promoted catalytic asymmetric annulation processes

Emily R. T. Robinson; Charlene Fallan; Carmen Simal; Alexandra M. Z. Slawin; Andrew D. Smith

doi:10.1039/c3sc50199j

Anhydrides as α,β-unsaturated acyl ammonium precursors: isothiourea-promoted catalytic asymmetric annulation processes

Emily R. T. Robinson, Charlene Fallan, Carmen Simal, Alexandra M. Z. Slawin, Andrew D. Smith^*

^*Corresponding author for this work

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

Abstract

The asymmetric annulation of a range of alpha,beta-unsaturated acyl ammonium intermediates, formed from isothiourea HBTM 2.1 and anhydrides with either 1,3-dicarbonyls, beta-ketoesters or azaaryl ketones gives either functionalised esters (upon ring opening), dihydropyranones or dihydropyridones in good yields (up to 93%) and high enantioselectivity (up to 97% ee).

Original language	English
Pages (from-to)	2193-2200
Number of pages	8
Journal	Chemical Science
Volume	4
Early online date	1 Mar 2013
DOIs	https://doi.org/10.1039/c3sc50199j
Publication status	Published - 2013

Keywords

Bicyclic-beta-lactones
Secondary benzylic alcohols
Dynamic kinetic resolution
N-heterocyclic carbenes
Silyl ketene acetals
Lewis-base catalysis
Enantioselective synthesis

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c3sc50199j
© Royal Society of Chemistry 2013. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
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title = "Anhydrides as α,β-unsaturated acyl ammonium precursors: isothiourea-promoted catalytic asymmetric annulation processes ",

abstract = "The asymmetric annulation of a range of alpha,beta-unsaturated acyl ammonium intermediates, formed from isothiourea HBTM 2.1 and anhydrides with either 1,3-dicarbonyls, beta-ketoesters or azaaryl ketones gives either functionalised esters (upon ring opening), dihydropyranones or dihydropyridones in good yields (up to 93%) and high enantioselectivity (up to 97% ee).",

keywords = "Bicyclic-beta-lactones, Secondary benzylic alcohols, Dynamic kinetic resolution, N-heterocyclic carbenes, Silyl ketene acetals, Lewis-base catalysis, Enantioselective synthesis",

author = "Robinson, {Emily R. T.} and Charlene Fallan and Carmen Simal and Slawin, {Alexandra M. Z.} and Smith, {Andrew D.}",

year = "2013",

doi = "10.1039/c3sc50199j",

language = "English",

volume = "4",

pages = "2193--2200",

journal = "Chemical Science",

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publisher = "Royal Society of Chemistry",

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T1 - Anhydrides as α,β-unsaturated acyl ammonium precursors

T2 - isothiourea-promoted catalytic asymmetric annulation processes

AU - Robinson, Emily R. T.

AU - Fallan, Charlene

AU - Simal, Carmen

AU - Slawin, Alexandra M. Z.

AU - Smith, Andrew D.

PY - 2013

Y1 - 2013

N2 - The asymmetric annulation of a range of alpha,beta-unsaturated acyl ammonium intermediates, formed from isothiourea HBTM 2.1 and anhydrides with either 1,3-dicarbonyls, beta-ketoesters or azaaryl ketones gives either functionalised esters (upon ring opening), dihydropyranones or dihydropyridones in good yields (up to 93%) and high enantioselectivity (up to 97% ee).

AB - The asymmetric annulation of a range of alpha,beta-unsaturated acyl ammonium intermediates, formed from isothiourea HBTM 2.1 and anhydrides with either 1,3-dicarbonyls, beta-ketoesters or azaaryl ketones gives either functionalised esters (upon ring opening), dihydropyranones or dihydropyridones in good yields (up to 93%) and high enantioselectivity (up to 97% ee).

KW - Bicyclic-beta-lactones

KW - Secondary benzylic alcohols

KW - Dynamic kinetic resolution

KW - N-heterocyclic carbenes

KW - Silyl ketene acetals

KW - Lewis-base catalysis

KW - Enantioselective synthesis

U2 - 10.1039/c3sc50199j

DO - 10.1039/c3sc50199j

M3 - Article

SN - 2041-6520

VL - 4

SP - 2193

EP - 2200

JO - Chemical Science

JF - Chemical Science

ER -

Anhydrides as α,β-unsaturated acyl ammonium precursors: isothiourea-promoted catalytic asymmetric annulation processes

Abstract

Keywords

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