Synthesis of α-Prolinols and 2-Amino-1,5-diols from Primary Nitroalkanes and Other Simple Precursors via Intermediacy of 5,6-Dihydro-4H-1,2-oxa­zines

Dedicated to Prof. Dr. H. Mayr on the occasion of his 65^th birthday

Abstract

A new strategy for the synthesis of 2-(1-hydroxy­alkyl)pyrrolidines and 2-amino-1,5-diols is suggested. The target compounds can be obtained in high yields from available precursors through the intermediacy of six-membered cyclic nitronates and their rearrangement products. Successive reduction of the latter led to the target products with moderate to high diastereoselectivity.

Key words

diastereoselective reduction - hydrogenation - 1,2-oxazine derivatives - amino alcohols - nitrones

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