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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• 作者：Airat M. Gimazetdinov^a ; ^{gimazetdinov@anrb.ru} ; Salavat S. Gataullin^a ; Ivan S. Bushmarinov^b ; Mansur S. Miftakhov^a
• 关键词：(+)-¦Á-Methylbenzylamine ; Chiral auxiliary ; ¦Ã-Lactones ; Cyclopentene block-synthons ; Optical resolution
• 刊名：Tetrahedron
• 出版年：2012
• 出版时间：22 July, 2012
• 年：2012
• 卷：68
• 期：29
• 页码：5754-5758
• 全文大小：292 K

文摘

Diastereomeric amides produced via the cleavage of easily available (¡À)-7,7-dichloro-4-exo-trimethylsilylbicyclo[3.2.0]hept-2-en-6-one by treatment with (+)-¦Á-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-cyclopenta[c]furan-1-ones after the removal of the chiral auxiliary and epoxidation.