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A General Procedure for the Synthesis of Enones via Gold-Catalyzed Meyer-Schuster Rearrangement of Propargylic Alcohols at Room Temperature

Pennell, MN; Unthank, MG; Turner, P; Sheppard, TD; (2011) A General Procedure for the Synthesis of Enones via Gold-Catalyzed Meyer-Schuster Rearrangement of Propargylic Alcohols at Room Temperature. J ORG CHEM , 76 (5) 1479 - 1482. 10.1021/jo102263t.

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Abstract

Meyer Schuster rearrangements of propargylic alcohols take place readily at room temperature in toluene with 1-2 mol PPh3AuNTf2, in the presence of 0.2 equiv of 4-methoxyphenylboronic acid or 1 equiv of methanol. Good to excellent yields of enones can be obtained from secondary and tertiary alcohols, with high selectivity for the E-alkene in most cases. A one-pot procedure for the conversion of primary propargylic alcohols into beta-arylketones was also developed, via Meyer-Schuster rearrangement followed by Pd-catalayzed addition of a boronic acid.

Type: Article
Title: A General Procedure for the Synthesis of Enones via Gold-Catalyzed Meyer-Schuster Rearrangement of Propargylic Alcohols at Room Temperature
DOI: 10.1021/jo102263t
Keywords: ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS, ORGANIC-REACTIONS, KETONES, OLEFINATION, PROSTAGLANDINS, ISOMERIZATION, ACTIVATION, CARBINOLS, COMPLEXES, ALDEHYDES
UCL classification: UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: http://discovery.ucl.ac.uk/id/eprint/1301706
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