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

Aqeel Ahmed; Patrick H. Dussault

doi:10.1021/ol048484h

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

Aqeel Ahmed, Patrick H. Dussault

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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 language	English (US)
Pages (from-to)	3609-3611
Number of pages	3
Journal	Organic Letters
Volume	6
Issue number	20
DOIs	https://doi.org/10.1021/ol048484h
State	Published - Sep 30 2004

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol048484h

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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.",

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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.

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

Abstract

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