Synthesis of Enantioenriched α,α-Disubstituted Cyclopentenes Catalyzed by N-Heterocyclic Carbenes

Overview

Journal Synthesis (Stuttg)

Publisher Thieme

Specialty Chemistry

Date 2011 Sep 28

PMID 21085623

Citations 6

Authors

Eric M Phillips

Manabu Wadamoto

Karl A Scheidt

Affiliations

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Abstract

The desymmetrization of 1,3-diketones using N-heterocyclic carbenes results in the formation of highly enantioenriched cyclopentenes in good yield. The reaction proceeds through a catalytic intramolecular aldol reaction and subsequent β-lactone formation. The expulsion of carbon dioxide at mild reaction temperatures affords the cyclopentene products.

Citing Articles

Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by -Heterocyclic Carbene Catalysis.

Johnston R, Cohen D, Eichman C, Scheidt K, Cheong P Chem Sci. 2014; 5(5):1974-1982.

PMID: 25045464 PMC: 4096939. DOI: 10.1039/C4SC00317A.

Exploiting Acyl and Enol Azolium Intermediates via NHeterocyclic Carbene Catalyzed Reactions of Alpha-Reducible Aldehydes.

Vora H, Wheeler P, Rovis T Adv Synth Catal. 2013; 354(9):1617-1639.

PMID: 23538785 PMC: 3607462. DOI: 10.1002/adsc.201200031.

Catalytic dynamic kinetic resolutions with N-heterocyclic carbenes: asymmetric synthesis of highly substituted β-lactones.

Cohen D, Eichman C, Phillips E, Zarefsky E, Scheidt K Angew Chem Int Ed Engl. 2012; 51(29):7309-13.

PMID: 22700327 PMC: 3489928. DOI: 10.1002/anie.201203382.

Discovering New Reactions with N-Heterocyclic Carbene Catalysis.

Phillips E, Chan A, Scheidt K Aldrichimica Acta. 2011; 42(3):55-66.

PMID: 21072130 PMC: 2975109.

Double diastereoselective, nucleophile-catalyzed aldol lactonizations (NCAL) leading to beta-lactone fused carbocycles and extensions to beta-lactone fused tetrahydrofurans.

Morris K, Arendt K, Oh S, Romo D Org Lett. 2010; 12(17):3764-7.

PMID: 20704184 PMC: 2933739. DOI: 10.1021/ol101388h.

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