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Abstract The report presents a first example of a regio- and stereospecific Lewis acid-catalyzed aminolysis of 1-benzyl-3,4-epoxypiperidine leading to trans -3-amino-1-benzylpiperidin-4-ols, in contrast with other Lewis acid-catalyzed reactions leading to… Click to show full abstract
Abstract The report presents a first example of a regio- and stereospecific Lewis acid-catalyzed aminolysis of 1-benzyl-3,4-epoxypiperidine leading to trans -3-amino-1-benzylpiperidin-4-ols, in contrast with other Lewis acid-catalyzed reactions leading to trans -4-amino-1-benzylpiperidin-3-ols. The reaction is performed at room temperature using the reagents prepared by interaction of a hard Lewis acid – diisobutylaluminum hydride (DIBAL-H) with primary and secondary amines. The obtained products are potential intermediates on the way to stereochemical analogues of the antitumor piperidine alkaloid pseudodistomin D .
Journal Title: Tetrahedron Letters
Year Published: 2017
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