alpha-Ketophosphonates as ester surrogates: isothiourea-catalyzed asymmetric diester and lactone synthesis

Siobhan R. Smith; Stuart M. Leckie; Reuben Holmes; James Douglas; Charlene Fallan; Peter Shapland; David Pryde; Alexandra M. Z. Slawin; Andrew D. Smith

doi:10.1021/ol500873s

alpha-Ketophosphonates as ester surrogates: isothiourea-catalyzed asymmetric diester and lactone synthesis

Siobhan R. Smith, Stuart M. Leckie, Reuben Holmes, James Douglas, Charlene Fallan, Peter Shapland, David Pryde, Alexandra M. Z. Slawin, Andrew D. Smith^*

^*Corresponding author for this work

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

45 Citations (Scopus)

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Abstract

Isothiourea HBTM-2.1 catalyzes the asymmetric Michael addition/lactonization of aryl- and alkenylacetic acids using α-keto-β,γ-unsaturated phosphonates as α,β-unsaturated ester surrogates, giving access to a diverse range of stereodefined lactones or
enantioenriched functionalized diesters upon ring-opening.

Original language	English
Pages (from-to)	2506-2509
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	9
Early online date	15 Apr 2014
DOIs	https://doi.org/10.1021/ol500873s
Publication status	Published - 2 May 2014

Keywords

Bicyclic-beta-lactones
Bis(oxazolinyl)pyridine-scandium(III) triflate complexes
Friedel-Crafts alkylations
Acyl transfer catalyst
Diels-Alder reactions
Aldol-Lactonization
Dyotropic Rearrangements
Keto Acids
Organocatalysis
Michael

Access to Document

10.1021/ol500873s

Smith_2014_OL_Alpha-Ketophosphonates_AM
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © 2014 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol500873s
Accepted author manuscript, 948 KB

RS Uni Research Fellowship Renewal 2010: University Research Fellowship - Cabranes ans Lewis Bases as Organocatalysts Synthetic Applications
Smith, A. D. (PI)
The Royal Society
1/10/10 → 30/09/13
Project: Fellowship

Cite this

@article{a25bc37a254545a5b1092762f5b35571,

title = "alpha-Ketophosphonates as ester surrogates: isothiourea-catalyzed asymmetric diester and lactone synthesis",

abstract = "Isothiourea HBTM-2.1 catalyzes the asymmetric Michael addition/lactonization of aryl- and alkenylacetic acids using α-keto-β,γ-unsaturated phosphonates as α,β-unsaturated ester surrogates, giving access to a diverse range of stereodefined lactones or enantioenriched functionalized diesters upon ring-opening.",

keywords = "Bicyclic-beta-lactones, Bis(oxazolinyl)pyridine-scandium(III) triflate complexes, Friedel-Crafts alkylations, Acyl transfer catalyst, Diels-Alder reactions, Aldol-Lactonization, Dyotropic Rearrangements, Keto Acids, Organocatalysis, Michael",

author = "Smith, {Siobhan R.} and Leckie, {Stuart M.} and Reuben Holmes and James Douglas and Charlene Fallan and Peter Shapland and David Pryde and Slawin, {Alexandra M. Z.} and Smith, {Andrew D.}",

note = "This work is in part supported by the European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 ",

year = "2014",

month = may,

day = "2",

doi = "10.1021/ol500873s",

language = "English",

volume = "16",

pages = "2506--2509",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "9",

}

TY - JOUR

T1 - alpha-Ketophosphonates as ester surrogates

T2 - isothiourea-catalyzed asymmetric diester and lactone synthesis

AU - Smith, Siobhan R.

AU - Leckie, Stuart M.

AU - Holmes, Reuben

AU - Douglas, James

AU - Fallan, Charlene

AU - Shapland, Peter

AU - Pryde, David

AU - Slawin, Alexandra M. Z.

AU - Smith, Andrew D.

N1 - This work is in part supported by the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850

PY - 2014/5/2

Y1 - 2014/5/2

N2 - Isothiourea HBTM-2.1 catalyzes the asymmetric Michael addition/lactonization of aryl- and alkenylacetic acids using α-keto-β,γ-unsaturated phosphonates as α,β-unsaturated ester surrogates, giving access to a diverse range of stereodefined lactones or enantioenriched functionalized diesters upon ring-opening.

AB - Isothiourea HBTM-2.1 catalyzes the asymmetric Michael addition/lactonization of aryl- and alkenylacetic acids using α-keto-β,γ-unsaturated phosphonates as α,β-unsaturated ester surrogates, giving access to a diverse range of stereodefined lactones or enantioenriched functionalized diesters upon ring-opening.

KW - Bicyclic-beta-lactones

KW - Bis(oxazolinyl)pyridine-scandium(III) triflate complexes

KW - Friedel-Crafts alkylations

KW - Acyl transfer catalyst

KW - Diels-Alder reactions

KW - Aldol-Lactonization

KW - Dyotropic Rearrangements

KW - Keto Acids

KW - Organocatalysis

KW - Michael

U2 - 10.1021/ol500873s

DO - 10.1021/ol500873s

M3 - Article

SN - 1523-7060

VL - 16

SP - 2506

EP - 2509

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

alpha-Ketophosphonates as ester surrogates: isothiourea-catalyzed asymmetric diester and lactone synthesis

Abstract

Keywords

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Projects

RS Uni Research Fellowship Renewal 2010: University Research Fellowship - Cabranes ans Lewis Bases as Organocatalysts Synthetic Applications

Cite this