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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
Author(s) -
Targel Tom,
Ramesh Palakuri,
Portnoy Moshe
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800380
Subject(s) - chemistry , hemiacetal , domino , alkoxy group , reagent , stoichiometry , organic chemistry , cascade reaction , catalysis , combinatorial chemistry , alkyl
Primary and secondary β‐alkoxy alcohols can be cleanly and efficiently oxidized into hemiacetal esters in a cascade two‐step process. m CPBA 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.