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Gold (III) Chloride-Catalyzed 6-endo-trig Oxa-Michael Addition Reactions for Diastereoselective Synthesis of Fused Tetrahydropyranones.

ABSTRACT: Alkynones were treated with boron trifluoride diethyl etherate to generate ?-iodoallenolates, which underwent intramolecular aldol reactions to produce cycloalkenyl alcohols. Diastereoselective oxa-Michael ring closure could then be induced by treatment with a catalytic amount of gold(III) chloride, affording highly functionalized tetrahydropyran-containing ring systems.

SUBMITTER: Ciesielski J

PROVIDER: S-EPMC3767299 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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Gold (III) Chloride-Catalyzed 6-endo-trig Oxa-Michael Addition Reactions for Diastereoselective Synthesis of Fused Tetrahydropyranones.

Ciesielski Jennifer J Lebœuf David D Stern Harry A HA Frontier Alison J AJ

Advanced synthesis & catalysis 20130701 10

Alkynones were treated with boron trifluoride diethyl etherate to generate β-iodoallenolates, which underwent intramolecular aldol reactions to produce cycloalkenyl alcohols. Diastereoselective oxa-Michael ring closure could then be induced by treatment with a catalytic amount of gold(III) chloride, affording highly functionalized tetrahydropyran-containing ring systems. ...[more]

PMID: 24032002

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