Asymmetric synthesis of tri- and tetrasubstituted trifluoromethyl dihydropyranones from alpha-aroyloxyaldehydes via NHC redox catalysis

Alyn T. Davies; Philip M. Pickett; Alexandra M. Z. Slawin; Andrew D. Smith

doi:10.1021/cs500667g

Asymmetric synthesis of tri- and tetrasubstituted trifluoromethyl dihydropyranones from alpha-aroyloxyaldehydes via NHC redox catalysis

Alyn T. Davies
, Philip M. Pickett
, Alexandra M. Z. Slawin
, Andrew D. Smith^*

^*Corresponding author for this work

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

Abstract

The asymmetric synthesis of tri- and tetrasubstituted trifluoromethyl dihydropyranones via an NHC-catalyzed redox process, introducing methyl, benzyl, and aryl substituents to the C(5) position, is presented. Their substrate-controlled derivatization into δ-lactones and cyclic hemiacetals containing stereogenic trifluoromethyl groups is also described.

Original language	English
Pages (from-to)	2696-2700
Number of pages	5
Journal	ACS Catalysis
Volume	4
Issue number	8
Early online date	15 Jul 2014
DOIs	https://doi.org/10.1021/cs500667g
Publication status	Published - Aug 2014

Keywords

Asymmetric organocatalysis
N-heterocyclic carbenes
Cycloaddition
Trifluoromethyl
Dihydropyranones
Delta-lactones
Diels-alder reactions
One-pot synthesis
Enantioselective synthesis
Fused dihydropyranones
Medicinal chemistry
4+2 Cycloaddition
Aldehydes
Ketenes
Functionalization

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10.1021/cs500667g

Smith_2014_ACSC_Asymmetric_AM
This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, 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/cs500667g
Accepted author manuscript, 1.05 MB

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Developing α-aroyloxyaldehydes as azolium enolate precursors in N-heterocyclic carbene organocatalysis
Davies, A. (Author), Smith, A. D. (Supervisor), 22 Jun 2016
Student thesis: Doctoral Thesis (PhD)

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title = "Asymmetric synthesis of tri- and tetrasubstituted trifluoromethyl dihydropyranones from alpha-aroyloxyaldehydes via NHC redox catalysis",

abstract = "The asymmetric synthesis of tri- and tetrasubstituted trifluoromethyl dihydropyranones via an NHC-catalyzed redox process, introducing methyl, benzyl, and aryl substituents to the C(5) position, is presented. Their substrate-controlled derivatization into δ-lactones and cyclic hemiacetals containing stereogenic trifluoromethyl groups is also described.",

keywords = "Asymmetric organocatalysis, N-heterocyclic carbenes, Cycloaddition, Trifluoromethyl, Dihydropyranones, Delta-lactones, Diels-alder reactions, One-pot synthesis, Enantioselective synthesis, Fused dihydropyranones, Medicinal chemistry, 4+2 Cycloaddition, Aldehydes, Ketenes, Functionalization",

author = "Davies, \{Alyn T.\} and Pickett, \{Philip M.\} and Slawin, \{Alexandra M. Z.\} and Smith, \{Andrew D.\}",

note = "We thank the Royal Society for a University Research Fellowship (A.D.S.), and the European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 (A.T.D.).",

year = "2014",

month = aug,

doi = "10.1021/cs500667g",

language = "English",

volume = "4",

pages = "2696--2700",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society (ACS)",

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T1 - Asymmetric synthesis of tri- and tetrasubstituted trifluoromethyl dihydropyranones from alpha-aroyloxyaldehydes via NHC redox catalysis

AU - Davies, Alyn T.

AU - Pickett, Philip M.

AU - Slawin, Alexandra M. Z.

AU - Smith, Andrew D.

N1 - We thank the Royal Society for a University Research Fellowship (A.D.S.), and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 (A.T.D.).

PY - 2014/8

Y1 - 2014/8

N2 - The asymmetric synthesis of tri- and tetrasubstituted trifluoromethyl dihydropyranones via an NHC-catalyzed redox process, introducing methyl, benzyl, and aryl substituents to the C(5) position, is presented. Their substrate-controlled derivatization into δ-lactones and cyclic hemiacetals containing stereogenic trifluoromethyl groups is also described.

AB - The asymmetric synthesis of tri- and tetrasubstituted trifluoromethyl dihydropyranones via an NHC-catalyzed redox process, introducing methyl, benzyl, and aryl substituents to the C(5) position, is presented. Their substrate-controlled derivatization into δ-lactones and cyclic hemiacetals containing stereogenic trifluoromethyl groups is also described.

KW - Asymmetric organocatalysis

KW - N-heterocyclic carbenes

KW - Cycloaddition

KW - Trifluoromethyl

KW - Dihydropyranones

KW - Delta-lactones

KW - Diels-alder reactions

KW - One-pot synthesis

KW - Enantioselective synthesis

KW - Fused dihydropyranones

KW - Medicinal chemistry

KW - 4+2 Cycloaddition

KW - Aldehydes

KW - Ketenes

KW - Functionalization

U2 - 10.1021/cs500667g

DO - 10.1021/cs500667g

M3 - Article

SN - 2155-5435

VL - 4

SP - 2696

EP - 2700

JO - ACS Catalysis

JF - ACS Catalysis

IS - 8

ER -

Asymmetric synthesis of tri- and tetrasubstituted trifluoromethyl dihydropyranones from alpha-aroyloxyaldehydes via NHC redox catalysis

Abstract

Keywords

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Student theses

Developing α-aroyloxyaldehydes as azolium enolate precursors in N-heterocyclic carbene organocatalysis

Cite this