Convenient synthesis of trans-3-amino-1-benzylpiperidin-4-ols using regiospecific cleavage of 1-benzyl-3,4-epoxypiperidine with diisobutylaluminum amides (DIBAL-NR1R2)статья
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Дата последнего поиска статьи во внешних источниках: 13 июня 2017 г.
Аннотация:The report presents a first example of a regio- and stereospecific Lewis acid-catalyzedaminolysis 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 reagentsprepared by interaction of a hard Lewis acid - diisobutylaluminum hydride (DIBAL-H) withprimary and secondary amines. The obtained products are potential intermediates on the wayto stereochemical analogues of the antitumor piperidine alkaloid pseudodistomin D.