Alkene dioxygenation with malonoyl peroxides: synthesis of ɣ-lactones, isobenzofuranones and tetrahydrofurans

Carla Alamillo-Ferrer, Marianna Karabourniotis-Sotti, Alan R. Kennedy, Matthew Campbell, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Treatment of homoallylic alcohols or carboxylic acids with malonoyl peroxide 1 provides a stereoselective method for the preparation of tetrahydrofurans, ɣ-lactones and isobenzofuranones in 44–82% yield and up to 27:1 trans-selectivity. Application of this simple and effective heterocyclization in the synthesis of the antidepressant citalopram is also described.
LanguageEnglish
Number of pages5
JournalOrganic Letters
Early online date17 Jun 2016
DOIs
Publication statusE-pub ahead of print - 17 Jun 2016

Fingerprint

Furans
Citalopram
Peroxides
Alkenes
peroxides
Lactones
tetrahydrofuran
Carboxylic Acids
carboxylic acids
Antidepressive Agents
alkenes
alcohols
selectivity
Alcohols
preparation
acids
synthesis

Keywords

  • saturated oxygen heterocycles
  • homoallylic alcohols
  • carboxylic acids

Cite this

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abstract = "Treatment of homoallylic alcohols or carboxylic acids with malonoyl peroxide 1 provides a stereoselective method for the preparation of tetrahydrofurans, ɣ-lactones and isobenzofuranones in 44–82{\%} yield and up to 27:1 trans-selectivity. Application of this simple and effective heterocyclization in the synthesis of the antidepressant citalopram is also described.",
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doi = "10.1021/acs.orglett.6b01253",
language = "English",
journal = "Organic Letters",
issn = "1523-7060",
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Alkene dioxygenation with malonoyl peroxides : synthesis of ɣ-lactones, isobenzofuranones and tetrahydrofurans. / Alamillo-Ferrer, Carla; Karabourniotis-Sotti, Marianna; Kennedy, Alan R.; Campbell, Matthew; Tomkinson, Nicholas C. O.

In: Organic Letters, 17.06.2016.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Alkene dioxygenation with malonoyl peroxides

T2 - Organic Letters

AU - Alamillo-Ferrer, Carla

AU - Karabourniotis-Sotti, Marianna

AU - Kennedy, Alan R.

AU - Campbell, Matthew

AU - Tomkinson, Nicholas C. O.

PY - 2016/6/17

Y1 - 2016/6/17

N2 - Treatment of homoallylic alcohols or carboxylic acids with malonoyl peroxide 1 provides a stereoselective method for the preparation of tetrahydrofurans, ɣ-lactones and isobenzofuranones in 44–82% yield and up to 27:1 trans-selectivity. Application of this simple and effective heterocyclization in the synthesis of the antidepressant citalopram is also described.

AB - Treatment of homoallylic alcohols or carboxylic acids with malonoyl peroxide 1 provides a stereoselective method for the preparation of tetrahydrofurans, ɣ-lactones and isobenzofuranones in 44–82% yield and up to 27:1 trans-selectivity. Application of this simple and effective heterocyclization in the synthesis of the antidepressant citalopram is also described.

KW - saturated oxygen heterocycles

KW - homoallylic alcohols

KW - carboxylic acids

UR - http://pubs.acs.org/loi/orlef7

U2 - 10.1021/acs.orglett.6b01253

DO - 10.1021/acs.orglett.6b01253

M3 - Article

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

ER -