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Direct transformation of 2,3-epoxy alcohols into hydroxy carbonates under mildly basic conditions

✍ Scribed by Andrew G. Myers; Katherine L. Widdowson

Book ID
104217795
Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
278 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

2,3-Epoxy alcohols are transformed into the corresponding C2-inverted hydroxy carbonates upon treatment with cesium carbonate-powdered 3-A molecular sieves in N,N-dimethylformamide under one atmosphere of carbon dioxide at 23-78 oC. As part of a recent study we required a stereospecific method to transform the epoxy alcohols 1 and 2 into the hydroxy carbonates 3 and 4.1 Standard procedures, notably Lewis acid induced rearrangement of the corresponding phenyl urethane derivatives,2 led to intractable product mixtures with these substrates, presumably a consequence of arene-facilitated epoxide opening at Cl. McCombie and Metz recently described a similar

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