☆ 4.5 Article

Facile Bifunctional Addition of Lactones and Esters at Low Temperatures. The First Intermediates in Lactone/Ester Hydrogenations

ORGANOMETALLICS (2009)

Journal

ORGANOMETALLICS

Volume 28, Issue 8, Pages 2349-2351

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/om9002076

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Natural Sciences and Engineering Research Council of Canada
University of Alberta

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Abstract

The bifunctional addition of lactones/esters is unexpectedly facile at low temperatures. Catalytic hydrogenations of esters can be carried out under mild conditions, e.g. -20 degrees C under 4 atm of H-2, bur product inhibition slows these reactions over time.

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Recent Advances in the Transition Metal-Catalyzed Addition of Carboxylic Acids to Alkynes

Vittorio Cadierno

Summary: Recent developments in the metal-catalyzed hydrofunctionalization of alkynes with carboxylic acids are comprehensively reviewed in this study, with a focus on both inter- and intramolecular processes and their implications in the synthesis of natural products and biologically active molecules. This review also highlights the use of cascade processes for the assembly of complex heterocyclic compounds.

CURRENT ORGANIC CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Catalytic enantioselective synthesis of 1,4-dihydropyridines via the addition of C(1)-ammonium enolates to pyridinium salts

Calum McLaughlin, Jacqueline Bitai, Lydia J. Barber, Alexandra M. Z. Slawin, Andrew D. Smith

Summary: The regio- and stereoselective addition of C(1)-ammonium enolates to pyridinium salts allows the synthesis of enantioenriched 1,4-dihydropyridines, representing the first organocatalytic approach to pyridine dearomatisation. The solvent and base used in the reaction significantly affect product enantioselectivity, with toluene and DABCO providing the best results. Counterion nature also plays a role, with coordinating bromide or chloride substrates leading to higher product er.

CHEMICAL SCIENCE (2021)

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Article Chemistry, Multidisciplinary

A facile synthesis of (& PLUSMN;)-15-deoxy- increment 12,14-prostaglandin J2 methyl ester

Zaynutdin R. Makaev, Nikolay S. Vostrikov, Natalya K. Selezneva, Mansur S. Miftakhov

Summary: A simple and efficient synthesis of racemic 15-deoxy- increment 12,14- prostaglandin J2 methyl ester from readily available Corey lactone diol in a total of eleven steps was proposed. Standard methods were used to form a fused co-chain and then converted into PGJ2 methyl ester. The transformation to the target prostaglandin was achieved smoothly in TsOH-CH2Cl2 medium by converting the allylic alcohol moiety to an exocyclic diene substituent conjugated with the endocyclic enone system.

MENDELEEV COMMUNICATIONS (2023)

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Facile Bifunctional Addition of Lactones and Esters at Low Temperatures. The First Intermediates in Lactone/Ester Hydrogenations

Journal

ORGANOMETALLICS

Publisher

AMER CHEMICAL SOC

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Funding

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Recent Advances in the Transition Metal-Catalyzed Addition of Carboxylic Acids to Alkynes

Catalytic enantioselective synthesis of 1,4-dihydropyridines via the addition of C(1)-ammonium enolates to pyridinium salts

A facile synthesis of (& PLUSMN;)-15-deoxy- increment 12,14-prostaglandin J2 methyl ester

Facile Bifunctional Addition of Lactones and Esters at Low Temperatures. The First Intermediates in Lactone/Ester Hydrogenations

Journal

ORGANOMETALLICS

Publisher

AMER CHEMICAL SOC

Keywords

Categories

Funding

Ask authors/readers for more resources

Protocol

Reagent

Authors

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Reviews

Primary Rating

Secondary Ratings

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Recommended

Recent Advances in the Transition Metal-Catalyzed Addition of Carboxylic Acids to Alkynes

Catalytic enantioselective synthesis of 1,4-dihydropyridines via the addition of C(1)-ammonium enolates to pyridinium salts

A facile synthesis of (& PLUSMN;)-15-deoxy- increment 12,14-prostaglandin J2 methyl ester

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