1,2,4-Trioxepanes: Redox-cleavable protection for carbonyl groups

Aqeel Ahmed, Patrick H. Dussault

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

(Chemical Equation Presented) 1,2,4-trioxepanes, readily prepared and easily handled derivatives of aldehydes and ketones, are stable to a variety of synthetic conditions and yet easily deblocked with Zn/HOAc or Mg/MeOH to regenerate the parent carbonyl. Trioxepanes may provide an alternative to 1,3-dithianes for acid-stable protection of carbonyl groups.

Original languageEnglish (US)
Pages (from-to)3609-3611
Number of pages3
JournalOrganic Letters
Volume6
Issue number20
DOIs
StatePublished - Sep 30 2004

Fingerprint

Ketones
aldehydes
Aldehydes
ketones
Oxidation-Reduction
Derivatives
acids
Acids
1,3-dithiane

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

1,2,4-Trioxepanes : Redox-cleavable protection for carbonyl groups. / Ahmed, Aqeel; Dussault, Patrick H.

In: Organic Letters, Vol. 6, No. 20, 30.09.2004, p. 3609-3611.

Research output: Contribution to journalArticle

@article{5b9782d3b15f4e8fb83c8d073c6f7ee2,
title = "1,2,4-Trioxepanes: Redox-cleavable protection for carbonyl groups",
abstract = "(Chemical Equation Presented) 1,2,4-trioxepanes, readily prepared and easily handled derivatives of aldehydes and ketones, are stable to a variety of synthetic conditions and yet easily deblocked with Zn/HOAc or Mg/MeOH to regenerate the parent carbonyl. Trioxepanes may provide an alternative to 1,3-dithianes for acid-stable protection of carbonyl groups.",
author = "Aqeel Ahmed and Dussault, {Patrick H.}",
year = "2004",
month = "9",
day = "30",
doi = "10.1021/ol048484h",
language = "English (US)",
volume = "6",
pages = "3609--3611",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "20",

}

TY - JOUR

T1 - 1,2,4-Trioxepanes

T2 - Redox-cleavable protection for carbonyl groups

AU - Ahmed, Aqeel

AU - Dussault, Patrick H.

PY - 2004/9/30

Y1 - 2004/9/30

N2 - (Chemical Equation Presented) 1,2,4-trioxepanes, readily prepared and easily handled derivatives of aldehydes and ketones, are stable to a variety of synthetic conditions and yet easily deblocked with Zn/HOAc or Mg/MeOH to regenerate the parent carbonyl. Trioxepanes may provide an alternative to 1,3-dithianes for acid-stable protection of carbonyl groups.

AB - (Chemical Equation Presented) 1,2,4-trioxepanes, readily prepared and easily handled derivatives of aldehydes and ketones, are stable to a variety of synthetic conditions and yet easily deblocked with Zn/HOAc or Mg/MeOH to regenerate the parent carbonyl. Trioxepanes may provide an alternative to 1,3-dithianes for acid-stable protection of carbonyl groups.

UR - http://www.scopus.com/inward/record.url?scp=6444243043&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=6444243043&partnerID=8YFLogxK

U2 - 10.1021/ol048484h

DO - 10.1021/ol048484h

M3 - Article

C2 - 15387560

AN - SCOPUS:6444243043

VL - 6

SP - 3609

EP - 3611

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 20

ER -