Improved Nitroaldol Reactions and Reductive Routes to Vicinal Aminoalcohols

TLDR: In this article, a variety of protected vicinal nitroalcohols are described, as well as an efficient method for their reduction to the corresponding vicinal aminoalcohols 2, 4 and 6.

Abstract: Summary Regioselective and flexible procedures are described for the preparation of a variety of protected vicinal nitroalcohols 1, 3 and 5 (see Scheme 5), as is an efficient method for their reduction to the corresponding vicinal aminoalcohols 2, 4 and 6 Vicinal aminoalcohols have broad significance in organic chemistry Their synthetic importance can be seen in the Tcfeneau-Demjanov and related deam- inative semipinacol rearrangements [ 11, and their biological relevance in the structures of adrenalin and related mediators of the sympathetic nervous system [2] [3] All of the main synthetic routes to this functional class possess significant limitations to their use [3], particularly in terms of the attainable degree of regio- selectivity For example, the orientation of oxirane ring-opening by a N-nucleophile depends upon both the substitution pattern of the oxirane and the reaction conditions employed The modified osmylation method of