☆ 4.7 Article

Stereoselective α,α′-Annelation Reactions of 1,3-Dioxan-5-ones

JOURNAL OF ORGANIC CHEMISTRY (2010)

期刊

JOURNAL OF ORGANIC CHEMISTRY

卷 75, 期 21, 页码 7461-7464

出版社

AMER CHEMICAL SOC

DOI: 10.1021/jo101531b

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Chemistry, Organic

资金

EPSRC [GR/R20465/01]
University of Birmingham
King's College London
European Regional Development Fund (ERDF)
Engineering and Physical Sciences Research Council [EP/C543122/1] Funding Source: researchfish

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摘要

Pyrrolidine enamines derived from three 1,3-dioxan-5-ones undergo (alpha,alpha'-annelation reactions with methyl alpha-(bromomethyl)acrylate to produce bridged 2,4-dioxabicyclo[3.3.1]-nonane ring systems with complete stereocontrol. Stereochemical outcomes have been rationalized based on steric and stereoelectronic interactions in intermediate boat-like conformations of the 1,3-dioxane ring and subsequent kinetic protonation to set an axial ester group on the cyclohexanone ring. Base-mediated ester epimerization provides the stereochemical array found in the highly oxygenated cyclohexane ring of phyllaemblic acid and glochicoccins B and D.

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