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Superbase‐Promoted Selective Cascade Cyclization Reaction of 1,5‐Diketones with Acetylenes to Methylene‐6,8‐dioxabicyclo[3.2.1]octanes
Author(s) -
Schmidt Elena Yu.,
Bidusenko Ivan A.,
Protsuk Nadezhda I.,
Ushakov Igor A.,
Trofimov Boris A.
Publication year - 2013
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.201201700
Subject(s) - chemistry , diastereomer , superbase , methylene , stereoselectivity , cascade reaction , yield (engineering) , cascade , organic chemistry , medicinal chemistry , stereochemistry , catalysis , chromatography , materials science , metallurgy
1,5‐Diketones are readily cyclized in the presence of various alkali‐metal superbases with acetylenes at 70 °C in a one‐pot cascade reaction to give methylene‐6,8‐dioxabicyclo[3.2.1]octanes in up to 92 % yield. In the case of symmetrical 1,5‐diketones, only one diastereomer is formed, whereas unsymmetrical diketones afford two diastereomers in a ratio corresponding to that of the starting ketones. This result indicates the key cascade cyclization sequence is stereoselective.