Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition-Lactonizations

Dorine Belmessieri; Louis Christian Morrill; Carmen Simal Fernandez; Alexandra Martha Zoya Slawin; Andrew David Smith

doi:10.1021/ja109975c

Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition-Lactonizations

Dorine Belmessieri, Louis Christian Morrill, Carmen Simal Fernandez, Alexandra Martha Zoya Slawin, Andrew David Smith

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

Abstract

Tetramisole promotes the catalytic asymmetric intramolecular Michael addition-lactonization of a variety of enone acids, giving carbo- and heterocyclic products with high diastereo- and enantiocontrol (up to 99:1 dr, up to 99% ee) that are readily derivatized to afford functionalized indene and dihydrobenzofuran carboxylates. Chiral isothioureas also promote the catalytic asymmetric intermolecular Michael addition-lactonization of arylacetic acids and alpha-keto-beta,gamma,-unsaturated esters, giving anti-dihydropyranones with high diastereo- and enantiocontrol (up to 98:2 dr, up to 99% ee).

Original language	English
Pages (from-to)	2714-2720
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	133
Issue number	8
DOIs	https://doi.org/10.1021/ja109975c
Publication status	Published - 2 Mar 2011

Keywords

DIELS-ALDER REACTIONS
N-HETEROCYCLIC CARBENES
BICYCLIC-BETA-LACTONES
ACYL-TRANSFER CATALYST
SECONDARY BENZYLIC ALCOHOLS
HIGHLY ENANTIOSELECTIVE SYNTHESIS
EFFECTIVE KINETIC RESOLUTION
PROMOTED BIS-CYCLIZATIONS
DELTA-LACTONES
ALPHA,BETA-UNSATURATED ALDEHYDES

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10.1021/ja109975c

Cite this

@article{945f6d2ff8b346df9c145404114b8066,

title = "Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition-Lactonizations",

abstract = "Tetramisole promotes the catalytic asymmetric intramolecular Michael addition-lactonization of a variety of enone acids, giving carbo- and heterocyclic products with high diastereo- and enantiocontrol (up to 99:1 dr, up to 99\% ee) that are readily derivatized to afford functionalized indene and dihydrobenzofuran carboxylates. Chiral isothioureas also promote the catalytic asymmetric intermolecular Michael addition-lactonization of arylacetic acids and alpha-keto-beta,gamma,-unsaturated esters, giving anti-dihydropyranones with high diastereo- and enantiocontrol (up to 98:2 dr, up to 99\% ee).",

keywords = "DIELS-ALDER REACTIONS, N-HETEROCYCLIC CARBENES, BICYCLIC-BETA-LACTONES, ACYL-TRANSFER CATALYST, SECONDARY BENZYLIC ALCOHOLS, HIGHLY ENANTIOSELECTIVE SYNTHESIS, EFFECTIVE KINETIC RESOLUTION, PROMOTED BIS-CYCLIZATIONS, DELTA-LACTONES, ALPHA,BETA-UNSATURATED ALDEHYDES",

author = "Dorine Belmessieri and Morrill, \{Louis Christian\} and \{Simal Fernandez\}, Carmen and Slawin, \{Alexandra Martha Zoya\} and Smith, \{Andrew David\}",

year = "2011",

month = mar,

day = "2",

doi = "10.1021/ja109975c",

language = "English",

volume = "133",

pages = "2714--2720",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society (ACS)",

number = "8",

}

Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition-Lactonizations. / Belmessieri, Dorine; Morrill, Louis Christian; Simal Fernandez, Carmen et al.
In: Journal of the American Chemical Society, Vol. 133, No. 8, 02.03.2011, p. 2714-2720.

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

TY - JOUR

T1 - Organocatalytic Functionalization of Carboxylic Acids

T2 - Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition-Lactonizations

AU - Belmessieri, Dorine

AU - Morrill, Louis Christian

AU - Simal Fernandez, Carmen

AU - Slawin, Alexandra Martha Zoya

AU - Smith, Andrew David

PY - 2011/3/2

Y1 - 2011/3/2

N2 - Tetramisole promotes the catalytic asymmetric intramolecular Michael addition-lactonization of a variety of enone acids, giving carbo- and heterocyclic products with high diastereo- and enantiocontrol (up to 99:1 dr, up to 99% ee) that are readily derivatized to afford functionalized indene and dihydrobenzofuran carboxylates. Chiral isothioureas also promote the catalytic asymmetric intermolecular Michael addition-lactonization of arylacetic acids and alpha-keto-beta,gamma,-unsaturated esters, giving anti-dihydropyranones with high diastereo- and enantiocontrol (up to 98:2 dr, up to 99% ee).

AB - Tetramisole promotes the catalytic asymmetric intramolecular Michael addition-lactonization of a variety of enone acids, giving carbo- and heterocyclic products with high diastereo- and enantiocontrol (up to 99:1 dr, up to 99% ee) that are readily derivatized to afford functionalized indene and dihydrobenzofuran carboxylates. Chiral isothioureas also promote the catalytic asymmetric intermolecular Michael addition-lactonization of arylacetic acids and alpha-keto-beta,gamma,-unsaturated esters, giving anti-dihydropyranones with high diastereo- and enantiocontrol (up to 98:2 dr, up to 99% ee).

KW - DIELS-ALDER REACTIONS

KW - N-HETEROCYCLIC CARBENES

KW - BICYCLIC-BETA-LACTONES

KW - ACYL-TRANSFER CATALYST

KW - SECONDARY BENZYLIC ALCOHOLS

KW - HIGHLY ENANTIOSELECTIVE SYNTHESIS

KW - EFFECTIVE KINETIC RESOLUTION

KW - PROMOTED BIS-CYCLIZATIONS

KW - DELTA-LACTONES

KW - ALPHA,BETA-UNSATURATED ALDEHYDES

UR - https://www.scopus.com/pages/publications/79952269315

U2 - 10.1021/ja109975c

DO - 10.1021/ja109975c

M3 - Article

SN - 0002-7863

VL - 133

SP - 2714

EP - 2720

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 8

ER -

Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition-Lactonizations

Abstract

Keywords

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Applications of isothioureas in organocatalysis: kinetic resolution of secondary alcohols and intramolecular Michael addition-lactonisation

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Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition-Lactonizations

Abstract

Keywords

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Student theses

Applications of isothioureas in organocatalysis: kinetic resolution of secondary alcohols and intramolecular Michael addition-lactonisation

Cite this