Three-Step Synthesis of 3-Aminoseptanoside Derivatives by Using Lithiated Methoxyallene and δ-Siloxynitrones

Dedicated to Professor Grzegorz Mlostoń on the occasion of his 65^th birthday

Abstract

A three-step approach to enantiomerically pure 3-aminoseptanoside derivatives by addition of lithiated methoxyallene to δ-silylated aldopentose-derived nitrones, followed by Brønsted acid mediated cyclization and chemoselective N–O bond scission is presented. For the addition of the methoxyallene anion leading to 3,6-dihydro-1,2-oxazines, excellent syn-diastereoselectivities were observed in the case of d-xylose- and l-arabinose-derived nitrones, whereas the d-ribose analogue provided syn- and anti-configured products in an approximately 2:1 ratio. Subsequent proton-induced reactions provided the corresponding dimethyl ketals as kinetic products, which slowly converted into bicyclic oxepanoides formed in a highly cis-selective manner. The final reductive ring opening was performed in good yields by using an excess of samarium(II) iodide. With a selected compound it was demonstrated that this type of product is a suitable precursor for the preparation of polyfunctionalized oxepanopyrrolidine derivatives.

Key words

allenes - nitrones - heterocycles - 1,2-oxazines - oxepanes - septanosides

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