Trapping hemiacetals with phosphono substituted palladium π-allyl complexes for the synthesis of substituted cyclic ethers

Nongnuch Sutivisedsak; Surendra Dawadi; Christopher D. Spilling

doi:10.1016/j.tetlet.2015.01.050

Trapping hemiacetals with phosphono substituted palladium π-allyl complexes for the synthesis of substituted cyclic ethers

Nongnuch Sutivisedsak, Surendra Dawadi, Christopher D. Spilling

Medicinal Chemistry

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

2 Scopus citations

Abstract

Abstract Oxidation of hydroxy substituted phosphono allylic carbonates gave the aldehyde substituted phosphonates in good yield. Stereospecific palladium (0)-catalyzed cyclization in the presence of methanol or water gave acetal tetrahydrofuran and tetrahydropyran vinyl phosphonate products derived from hemiacetal trapping. The tetrahydrofuran acetals undergo Lewis acid catalyzed addition of nucleophiles to give diastereoisomeric mixtures of substituted tetrahydrofurans.

Original language	English (US)
Article number	45720
Pages (from-to)	3534-3537
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2015.01.050
State	Published - Dec 15 2015

Bibliographical note

Funding Information:
The project described was supported in part by grant number R01- GM076192 from the National Institute of General Medicine . We thank National Science Foundation for grants to purchase the NMR spectrometer (CHE-9974801), and the mass spectrometer (CHE-9708640). We thank Mr. Joe Kramer and Prof. R.E.K. Winter of the Department of Chemistry and Biochemistry, UMSL for mass spectra.

Publisher Copyright:
© 2015 Elsevier Ltd.

Keywords

Acetal
Allyl phosphonates
Catalysis
Cyclization
Palladium π-allyl
Vinyl phosphonates

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title = "Trapping hemiacetals with phosphono substituted palladium π-allyl complexes for the synthesis of substituted cyclic ethers",

abstract = "Abstract Oxidation of hydroxy substituted phosphono allylic carbonates gave the aldehyde substituted phosphonates in good yield. Stereospecific palladium (0)-catalyzed cyclization in the presence of methanol or water gave acetal tetrahydrofuran and tetrahydropyran vinyl phosphonate products derived from hemiacetal trapping. The tetrahydrofuran acetals undergo Lewis acid catalyzed addition of nucleophiles to give diastereoisomeric mixtures of substituted tetrahydrofurans.",

keywords = "Acetal, Allyl phosphonates, Catalysis, Cyclization, Palladium π-allyl, Vinyl phosphonates",

author = "Nongnuch Sutivisedsak and Surendra Dawadi and Spilling, {Christopher D.}",

note = "Funding Information: The project described was supported in part by grant number R01- GM076192 from the National Institute of General Medicine . We thank National Science Foundation for grants to purchase the NMR spectrometer (CHE-9974801), and the mass spectrometer (CHE-9708640). We thank Mr. Joe Kramer and Prof. R.E.K. Winter of the Department of Chemistry and Biochemistry, UMSL for mass spectra. Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd.",

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AU - Sutivisedsak, Nongnuch

AU - Dawadi, Surendra

AU - Spilling, Christopher D.

N1 - Funding Information: The project described was supported in part by grant number R01- GM076192 from the National Institute of General Medicine . We thank National Science Foundation for grants to purchase the NMR spectrometer (CHE-9974801), and the mass spectrometer (CHE-9708640). We thank Mr. Joe Kramer and Prof. R.E.K. Winter of the Department of Chemistry and Biochemistry, UMSL for mass spectra. Publisher Copyright: © 2015 Elsevier Ltd.

PY - 2015/12/15

Y1 - 2015/12/15

N2 - Abstract Oxidation of hydroxy substituted phosphono allylic carbonates gave the aldehyde substituted phosphonates in good yield. Stereospecific palladium (0)-catalyzed cyclization in the presence of methanol or water gave acetal tetrahydrofuran and tetrahydropyran vinyl phosphonate products derived from hemiacetal trapping. The tetrahydrofuran acetals undergo Lewis acid catalyzed addition of nucleophiles to give diastereoisomeric mixtures of substituted tetrahydrofurans.

AB - Abstract Oxidation of hydroxy substituted phosphono allylic carbonates gave the aldehyde substituted phosphonates in good yield. Stereospecific palladium (0)-catalyzed cyclization in the presence of methanol or water gave acetal tetrahydrofuran and tetrahydropyran vinyl phosphonate products derived from hemiacetal trapping. The tetrahydrofuran acetals undergo Lewis acid catalyzed addition of nucleophiles to give diastereoisomeric mixtures of substituted tetrahydrofurans.

KW - Acetal

KW - Allyl phosphonates

KW - Catalysis

KW - Cyclization

KW - Palladium π-allyl

KW - Vinyl phosphonates

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Trapping hemiacetals with phosphono substituted palladium π-allyl complexes for the synthesis of substituted cyclic ethers

Abstract

Bibliographical note

Keywords

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