A simple and efficient synthesis of enantiomeric (3aRS,4RS,6aSR)-4-hydroxy-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]furan-1-ones |
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| Authors: | Airat M Gimazetdinov Salavat S Gataullin Ivan S Bushmarinov Mansur S Miftakhov |
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| Institution: | 1. Institute of Organic Chemistry of Ufa Research Centre, Russian Academy of Sciences, Prospect Oktyabrya 71, 450054 Ufa, Russian Federation;2. A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str., 28, 119991 Moscow, Russian Federation |
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| Abstract: | Diastereomeric amides produced via the cleavage of easily available (±)-7,7-dichloro-4-exo-trimethylsilylbicyclo3.2.0]hept-2-en-6-one by treatment with (+)-α-methylbenzylamine were transformed into bicyclic lactam-aminals, which can easily be separated by column chromatography on SiO2. The latter products lead to enantiomeric (3a,6a)-4-hydroxy-3,3a,4,6a-tetrahydro-1H-cyclopentac]furan-1-ones after the removal of the chiral auxiliary and epoxidation. |
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