Intermolecular oxonium ylide mediated synthesis of medium-sized oxacycles

Daniel J. MacK, Lindsay A. Batory, Jon T Njardarson

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Detailed in this account are our efforts toward efficient oxacycle syntheses. Two complementary approaches are discussed, with both employing chemoselective allyl ether activation and rearrangement as the key step. Vinyl substituted oxiranes and oxetanes provide a single step access to dihydropyrans and tetrahydrooxepines. Oxiranes proved to be poor substrates, while oxetanes were slightly better. An alternative approach using substituted allyl ethers proved successful and addressed the limitations encountered in the ring expansions.

Original languageEnglish (US)
Pages (from-to)378-381
Number of pages4
JournalOrganic Letters
Volume14
Issue number1
DOIs
StatePublished - Jan 6 2012

Fingerprint

Epoxy Compounds
ethers
Ethers
synthesis
Ether
Chemical activation
activation
expansion
rings
Substrates
hydronium ion
oxetane
3,4-epoxy-1-butene

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Intermolecular oxonium ylide mediated synthesis of medium-sized oxacycles. / MacK, Daniel J.; Batory, Lindsay A.; Njardarson, Jon T.

In: Organic Letters, Vol. 14, No. 1, 06.01.2012, p. 378-381.

Research output: Contribution to journalArticle

MacK, Daniel J. ; Batory, Lindsay A. ; Njardarson, Jon T. / Intermolecular oxonium ylide mediated synthesis of medium-sized oxacycles. In: Organic Letters. 2012 ; Vol. 14, No. 1. pp. 378-381.
@article{afe17d3e4a6f43f3801e29b2bbb5176f,
title = "Intermolecular oxonium ylide mediated synthesis of medium-sized oxacycles",
abstract = "Detailed in this account are our efforts toward efficient oxacycle syntheses. Two complementary approaches are discussed, with both employing chemoselective allyl ether activation and rearrangement as the key step. Vinyl substituted oxiranes and oxetanes provide a single step access to dihydropyrans and tetrahydrooxepines. Oxiranes proved to be poor substrates, while oxetanes were slightly better. An alternative approach using substituted allyl ethers proved successful and addressed the limitations encountered in the ring expansions.",
author = "MacK, {Daniel J.} and Batory, {Lindsay A.} and Njardarson, {Jon T}",
year = "2012",
month = "1",
day = "6",
doi = "10.1021/ol203129d",
language = "English (US)",
volume = "14",
pages = "378--381",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "1",

}

TY - JOUR

T1 - Intermolecular oxonium ylide mediated synthesis of medium-sized oxacycles

AU - MacK, Daniel J.

AU - Batory, Lindsay A.

AU - Njardarson, Jon T

PY - 2012/1/6

Y1 - 2012/1/6

N2 - Detailed in this account are our efforts toward efficient oxacycle syntheses. Two complementary approaches are discussed, with both employing chemoselective allyl ether activation and rearrangement as the key step. Vinyl substituted oxiranes and oxetanes provide a single step access to dihydropyrans and tetrahydrooxepines. Oxiranes proved to be poor substrates, while oxetanes were slightly better. An alternative approach using substituted allyl ethers proved successful and addressed the limitations encountered in the ring expansions.

AB - Detailed in this account are our efforts toward efficient oxacycle syntheses. Two complementary approaches are discussed, with both employing chemoselective allyl ether activation and rearrangement as the key step. Vinyl substituted oxiranes and oxetanes provide a single step access to dihydropyrans and tetrahydrooxepines. Oxiranes proved to be poor substrates, while oxetanes were slightly better. An alternative approach using substituted allyl ethers proved successful and addressed the limitations encountered in the ring expansions.

UR - http://www.scopus.com/inward/record.url?scp=84855501603&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84855501603&partnerID=8YFLogxK

U2 - 10.1021/ol203129d

DO - 10.1021/ol203129d

M3 - Article

VL - 14

SP - 378

EP - 381

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 1

ER -