Intramolecular anodic olefin coupling reactions: The use of an allylic alkoxy group for controlling relative stereochemistry

Dean A. Frey; Jeffery A. Marx; Kevin D. Moeller

doi:10.1016/S0013-4686(97)85468-0

Intramolecular anodic olefin coupling reactions: The use of an allylic alkoxy group for controlling relative stereochemistry

Dean A. Frey, Jeffery A. Marx, Kevin D. Moeller

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

9 Scopus citations

Abstract

The study of intramolecular anodic olefin coupling reactions arising from diene substrates having an allylic alkoxy group have been studied. In all cases, the coupling reactions proceeded smoothly without elimination of the allylic alkoxy group. In addition, the reactions were found to afford five-membered ring products in a diastereoselective fashion. Substrates having both cis- and trans-disubstituted allyl silane olefin participants led to different ratios of products indicating that the cyclization reactions were under kinetic control.

Original language	English
Pages (from-to)	1967-1970
Number of pages	4
Journal	Electrochimica Acta
Volume	42
Issue number	13-14
DOIs	https://doi.org/10.1016/S0013-4686(97)85468-0
State	Published - 1997

Keywords

Intramolecular anodic olefin coupling
Stereochemistry

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10.1016/S0013-4686(97)85468-0

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title = "Intramolecular anodic olefin coupling reactions: The use of an allylic alkoxy group for controlling relative stereochemistry",

abstract = "The study of intramolecular anodic olefin coupling reactions arising from diene substrates having an allylic alkoxy group have been studied. In all cases, the coupling reactions proceeded smoothly without elimination of the allylic alkoxy group. In addition, the reactions were found to afford five-membered ring products in a diastereoselective fashion. Substrates having both cis- and trans-disubstituted allyl silane olefin participants led to different ratios of products indicating that the cyclization reactions were under kinetic control.",

keywords = "Intramolecular anodic olefin coupling, Stereochemistry",

author = "Frey, {Dean A.} and Marx, {Jeffery A.} and Moeller, {Kevin D.}",

note = "Funding Information: We thank the National Science Foundation (CHE-9023698)f or their generouss upport of this work. We also gratefullya cknowledgeth e Washington University High Resolution NMR facility, partially supported by NIH grants RR02004, RR05018, and RR07155 and the Washington University Mass SpectrometryR esource Center,",

year = "1997",

doi = "10.1016/S0013-4686(97)85468-0",

language = "English",

volume = "42",

pages = "1967--1970",

journal = "Electrochimica Acta",

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TY - JOUR

T1 - Intramolecular anodic olefin coupling reactions

T2 - The use of an allylic alkoxy group for controlling relative stereochemistry

AU - Frey, Dean A.

AU - Marx, Jeffery A.

AU - Moeller, Kevin D.

N1 - Funding Information: We thank the National Science Foundation (CHE-9023698)f or their generouss upport of this work. We also gratefullya cknowledgeth e Washington University High Resolution NMR facility, partially supported by NIH grants RR02004, RR05018, and RR07155 and the Washington University Mass SpectrometryR esource Center,

PY - 1997

Y1 - 1997

N2 - The study of intramolecular anodic olefin coupling reactions arising from diene substrates having an allylic alkoxy group have been studied. In all cases, the coupling reactions proceeded smoothly without elimination of the allylic alkoxy group. In addition, the reactions were found to afford five-membered ring products in a diastereoselective fashion. Substrates having both cis- and trans-disubstituted allyl silane olefin participants led to different ratios of products indicating that the cyclization reactions were under kinetic control.

AB - The study of intramolecular anodic olefin coupling reactions arising from diene substrates having an allylic alkoxy group have been studied. In all cases, the coupling reactions proceeded smoothly without elimination of the allylic alkoxy group. In addition, the reactions were found to afford five-membered ring products in a diastereoselective fashion. Substrates having both cis- and trans-disubstituted allyl silane olefin participants led to different ratios of products indicating that the cyclization reactions were under kinetic control.

KW - Intramolecular anodic olefin coupling

KW - Stereochemistry

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U2 - 10.1016/S0013-4686(97)85468-0

DO - 10.1016/S0013-4686(97)85468-0

M3 - Article

AN - SCOPUS:0030652690

SN - 0013-4686

VL - 42

SP - 1967

EP - 1970

JO - Electrochimica Acta

JF - Electrochimica Acta

IS - 13-14

ER -

Intramolecular anodic olefin coupling reactions: The use of an allylic alkoxy group for controlling relative stereochemistry

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