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

Publisher Copyright:
© 2015 Elsevier Ltd.

Keywords

Acetal
Allyl phosphonates
Catalysis
Cyclization
Palladium π-allyl
Vinyl phosphonates

Publisher link

10.1016/j.tetlet.2015.01.050

Find It

Find It at U of M Libraries

Cite this

@article{a5da53c13d594e9090f5fcc6e2a5daf4,

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 = "Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd.",

year = "2015",

month = dec,

day = "15",

doi = "10.1016/j.tetlet.2015.01.050",

language = "English (US)",

volume = "56",

pages = "3534--3537",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "23",

}

TY - JOUR

T1 - Trapping hemiacetals with phosphono substituted palladium π-allyl complexes for the synthesis of substituted cyclic ethers

AU - Sutivisedsak, Nongnuch

AU - Dawadi, Surendra

AU - Spilling, Christopher D.

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

UR - http://www.scopus.com/inward/record.url?scp=84939994184&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84939994184&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2015.01.050

DO - 10.1016/j.tetlet.2015.01.050

M3 - Article

AN - SCOPUS:84939994184

SN - 0040-4039

VL - 56

SP - 3534

EP - 3537

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

M1 - 45720

ER -

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

Abstract

Bibliographical note

Keywords

Publisher link

Find It

Other files and links

Fingerprint

Cite this