Work

Stereoselective Synthesis of Cyclic Ethers via the Palladium-Catalyzed Intramolecular Addition of Alcohols to Phosphono Allylic Carbonates

Year: 2009

Type: article

Abstract: Cross metathesis of the acrolein-derived phosphono allylic carbonate and hydroxy alkenes using second generation Grubbs catalyst and copper(I) iodide gave the substituted phosphonates in good yield. Stereospecific palladium(0)-catalyzed cyclization gave tetrahydrofuran and tetrahydropyran vinyl phosphonates. Regioselective Wacker oxidation of the vinyl phosphonate gave the beta-keto phosphonate, which underwent HWE reaction with benzaldehyde to yield the unsaturated ketone. The utility of the cross metathesis/cyclization protocol was further demonstrated by a formal synthesis of centrolobine.

Source: Organic Letters

DOI: 10.1021/ol900980s

Authors: Anyu He, Nongnuch Sutivisedsak, Christopher D. Spilling

Institution: University of Missouri–St. Louis

Language: English

Topic: Organophosphorus compounds synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Award: Tetrahydrofurans, Tetrahydropyrans and 2H-Furanones