Stereoselective synthesis of octahydro-3bH-[1,3]dioxolo[4″,5″:4′,5′]furo[2′,3′:5,6]pyrano[4,3-b]quinolines via intramolecular hetero-Diels–Alder

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• 作者：Sabitha ; Gowravaram ; Venkata Reddy ; E. ; Yadav ; J. S. ; Rama Krishna ; K. V. S. ; Ravi Sankar ; A.
• 关键词：hetero-Diels&ndash ; Alder reactions ; bismuth(III) chloride ; stereoselective ; furo-pyrano quinolines
• 刊名：Tetrahedron Letters
• 出版年：2002
• 出版时间：May 27, 2002
• 年：2002
• 卷：43
• 期：22
• 页码：4029-4032
• 全文大小：156 K

文摘

A new, efficient and stereoselective synthesis of furo[2′,3′:5,6]pyrano[4,3-b]quinoline derivatives 3 and 3′ has been achieved by intramolecular hetero–Diels–Alder reactions of aldimines generated in situ from aromatic amines and the O-allyl derivative of the chiral sugar derived aldehyde 2 in acetonitrile in the presence of a catalytic amount of BiCl₃. The products are formed with extremely high trans selectivity in good to excellent yields.