Domino Two-Step Oxidation of β-Alkoxy Alcohols to Hemiacetal Esters: Linking a Stoichiometric Step to an Organocatalytic Step with a Common Organic Oxidant

Tom Targel; Palakuri Ramesh; Moshe Portnoy

doi:10.1002/ejoc.201800380

Domino Two-Step Oxidation of β-Alkoxy Alcohols to Hemiacetal Esters: Linking a Stoichiometric Step to an Organocatalytic Step with a Common Organic Oxidant

Tom Targel, Palakuri Ramesh, Moshe Portnoy^*

^*Corresponding author for this work

School of Chemistry

Tel Aviv University

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

Primary and secondary β-alkoxy alcohols can be cleanly and efficiently oxidized into hemiacetal esters in a cascade two-step process. mCPBA serves both as a stoichiometric oxidant in the first TEMPO-catalyzed step, converting alcohols to aldehydes/ketones, and as a reagent in the second Baeyer–Villiger stoichiometric oxidation, transforming the aldehydes/ketones into hemiacetal esters. The use of an oxidant common to both steps enables the domino reaction to proceed under a single experimental setting. Longer oxidative cascade sequences are possible when this new methodology is applied to suitable substrates.

Original language	English
Pages (from-to)	3017-3021
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	23
DOIs	https://doi.org/10.1002/ejoc.201800380
State	Published - 22 Jun 2018

Funding

Funders	Funder number
United States-Israel Binational Science Foundation	2012193
Israel Science Foundation	955/10
Planning and Budgeting Committee of the Council for Higher Education of Israel

Keywords

Domino reactions
Hemiacetal esters
Organocatalysis
Oxidation
Synthetic methods

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10.1002/ejoc.201800380

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title = "Domino Two-Step Oxidation of β-Alkoxy Alcohols to Hemiacetal Esters: Linking a Stoichiometric Step to an Organocatalytic Step with a Common Organic Oxidant",

abstract = "Primary and secondary β-alkoxy alcohols can be cleanly and efficiently oxidized into hemiacetal esters in a cascade two-step process. mCPBA serves both as a stoichiometric oxidant in the first TEMPO-catalyzed step, converting alcohols to aldehydes/ketones, and as a reagent in the second Baeyer–Villiger stoichiometric oxidation, transforming the aldehydes/ketones into hemiacetal esters. The use of an oxidant common to both steps enables the domino reaction to proceed under a single experimental setting. Longer oxidative cascade sequences are possible when this new methodology is applied to suitable substrates.",

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AU - Ramesh, Palakuri

AU - Portnoy, Moshe

PY - 2018/6/22

Y1 - 2018/6/22

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AB - Primary and secondary β-alkoxy alcohols can be cleanly and efficiently oxidized into hemiacetal esters in a cascade two-step process. mCPBA serves both as a stoichiometric oxidant in the first TEMPO-catalyzed step, converting alcohols to aldehydes/ketones, and as a reagent in the second Baeyer–Villiger stoichiometric oxidation, transforming the aldehydes/ketones into hemiacetal esters. The use of an oxidant common to both steps enables the domino reaction to proceed under a single experimental setting. Longer oxidative cascade sequences are possible when this new methodology is applied to suitable substrates.

KW - Domino reactions

KW - Hemiacetal esters

KW - Organocatalysis

KW - Oxidation

KW - Synthetic methods

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Domino Two-Step Oxidation of β-Alkoxy Alcohols to Hemiacetal Esters: Linking a Stoichiometric Step to an Organocatalytic Step with a Common Organic Oxidant

Abstract

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