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Modular Synthesis of Dihydroxyacetone Monoalkyl Ethers and Isosteric 1‐Hydroxy‐2‐alkanones
Author(s) -
Güclü Deniz,
Rale Madhura,
Fessner WolfDieter
Publication year - 2015
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.201403695
Subject(s) - chemistry , glycidol , dihydroxyacetone , organic chemistry , alkylation , epoxide , catalysis , modular design , combinatorial chemistry , glycerol , computer science , operating system
Straightforward methods for the efficient, systematic preparation of libraries of the title compound classes have been evaluated. A general and efficient modular route to dihydroxyacetone monoethers was developed based on trityl glycidol, which, through epoxide opening, oxidation, and deprotection, provided variously alkylated ethers by three routine operations in good overall yields (eight examples, 24–59 %). The preparation of structurally related 1‐hydroxyalkanones depends on the availability of the most economic starting materials and on their physicochemical properties. Thus, the most practical one‐step approaches consisted of the sec ‐selective oxidation of short‐chain 1,2‐diols (≤ C 6 ) using NaOCl, and the direct ketohydroxylation of 1‐alkenes (≥ C 6 ) using buffered stoichiometric KMnO 4 or catalytic RuO 4 with reoxidation by oxone, for which mostly good overall yields were achieved on a multigram scale (nine examples, 15–78 %).