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Orthoester condensation/CO insertion reaction sequence for the preparation of tetrahydrofurans

✍ Scribed by Michael A. Calter; Priyantha M. Sugathapala

Book ID: 104260184
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 205 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01987-x

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✦ Synopsis

This paper describes a general procedure for the efficient preparation of highly substituted tetrahydrofurans. The condensation of ~-diazo-13-ketoester-derived enolates with orthoesters yields diazoacetals la-ld. These compounds undergo formal C-O insertion reactions in the presence of Rh2(OAc)4 to afford tetrahydrofurylacetals 2a-2c. Similar insertion reactions of diazoacetals 5a-5d yield bicyclic acetals 6a-6d, which possess cores similar to those of the zaragozic acids.

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