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

Anyu He; Nongnuch Sutivisedsak; Christopher D. Spilling

doi:10.1021/ol900980s

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

Anyu He
, Nongnuch Sutivisedsak
, Christopher D. Spilling

University of Missouri-St. Louis

Research output: Contribution to journal › Article › peer-review

Original language	American English
Journal	Organic Letters
Volume	11
DOIs	https://doi.org/10.1021/ol900980s
State	Published - Jul 16 2009

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Chemistry
Organic Chemistry

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@article{73780a80b58c45c0b5202891a1bd4d90,

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

author = "Anyu He and Nongnuch Sutivisedsak and Spilling, \{Christopher D.\}",

note = "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 β-keto phosphonate, which underwent HWE reaction with benzaldehyde to yield the unsaturated ketone.",

year = "2009",

month = jul,

day = "16",

doi = "10.1021/ol900980s",

language = "American English",

volume = "11",

journal = "Organic Letters",

}

TY - JOUR

T1 - Stereoselective Synthesis of Cyclic Ethers via the Palladium-Catalyzed Intramolecular Addition of Alcohols to Phosphono Allylic Carbonates

AU - He, Anyu

AU - Sutivisedsak, Nongnuch

AU - Spilling, Christopher D.

N1 - 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 β-keto phosphonate, which underwent HWE reaction with benzaldehyde to yield the unsaturated ketone.

PY - 2009/7/16

Y1 - 2009/7/16

UR - https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2717013/

U2 - 10.1021/ol900980s

DO - 10.1021/ol900980s

M3 - Article

VL - 11

JO - Organic Letters

JF - Organic Letters

ER -

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

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