Reaction of 1O2 with alkoxyallylstannanes: Synthesis of 1,2-dioxolanes and allyl hydroperoxides

P. H. Dussault, U. R. Zope

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The reaction of 1O2 with chiral alkoxyallylstannanes provides a new route for the stereoselective synthesis of 1,2-dioxolanes and allyl hydroperoxides. Dioxolane formation, which proceeds through ring opening of the intermediate perepoxide upon migration of the stannyl group, is shown to be favored by the presence of an electron-donating group and by steric factors suppressing the more typical H-ene reaction.

Original languageEnglish (US)
Pages (from-to)2187-2190
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number13
DOIs
StatePublished - Mar 27 1995

Fingerprint

Dioxolanes
Hydrogen Peroxide
Electrons
formal glycol

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Reaction of 1O2 with alkoxyallylstannanes : Synthesis of 1,2-dioxolanes and allyl hydroperoxides. / Dussault, P. H.; Zope, U. R.

In: Tetrahedron Letters, Vol. 36, No. 13, 27.03.1995, p. 2187-2190.

Research output: Contribution to journalArticle

@article{390aca5328d94442b1e23f5461a54871,
title = "Reaction of 1O2 with alkoxyallylstannanes: Synthesis of 1,2-dioxolanes and allyl hydroperoxides",
abstract = "The reaction of 1O2 with chiral alkoxyallylstannanes provides a new route for the stereoselective synthesis of 1,2-dioxolanes and allyl hydroperoxides. Dioxolane formation, which proceeds through ring opening of the intermediate perepoxide upon migration of the stannyl group, is shown to be favored by the presence of an electron-donating group and by steric factors suppressing the more typical H-ene reaction.",
author = "Dussault, {P. H.} and Zope, {U. R.}",
year = "1995",
month = "3",
day = "27",
doi = "10.1016/0040-4039(95)00231-Z",
language = "English (US)",
volume = "36",
pages = "2187--2190",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "13",

}

TY - JOUR

T1 - Reaction of 1O2 with alkoxyallylstannanes

T2 - Synthesis of 1,2-dioxolanes and allyl hydroperoxides

AU - Dussault, P. H.

AU - Zope, U. R.

PY - 1995/3/27

Y1 - 1995/3/27

N2 - The reaction of 1O2 with chiral alkoxyallylstannanes provides a new route for the stereoselective synthesis of 1,2-dioxolanes and allyl hydroperoxides. Dioxolane formation, which proceeds through ring opening of the intermediate perepoxide upon migration of the stannyl group, is shown to be favored by the presence of an electron-donating group and by steric factors suppressing the more typical H-ene reaction.

AB - The reaction of 1O2 with chiral alkoxyallylstannanes provides a new route for the stereoselective synthesis of 1,2-dioxolanes and allyl hydroperoxides. Dioxolane formation, which proceeds through ring opening of the intermediate perepoxide upon migration of the stannyl group, is shown to be favored by the presence of an electron-donating group and by steric factors suppressing the more typical H-ene reaction.

UR - http://www.scopus.com/inward/record.url?scp=0028907632&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028907632&partnerID=8YFLogxK

U2 - 10.1016/0040-4039(95)00231-Z

DO - 10.1016/0040-4039(95)00231-Z

M3 - Article

AN - SCOPUS:0028907632

VL - 36

SP - 2187

EP - 2190

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 13

ER -