Preparation and reactions of some 1-amino-1-deoxyheptitols

Richtmyer, Nelson K.

doi:10.1016/s0008-6215(00)81142-8

Cited by 2 publications

(1 citation statement)

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“…It is somewhat surprising that while the chemistry of reducing aminosugars, particularly 2-amino-2-deoxyaldoses, is well established, that of aminopolyols remains quite underexploited. Early preparations of 1-amino-1-deoxypolyols include catalytic hydrogenation in the presence of Pt, Pd, or Raney Ni of the corresponding glycosylamines or hydrazones, hydrogenation of 1-deoxy-1-nitropolyols over Ag 2 O, as well as chemical 3 or electrolytic reduction of monosaccharide oximes.…”

Section: Introductionmentioning

confidence: 99%

Chiral N-Acyloxazolidines: Synthesis, Structure, and Mechanistic Insights

et al. 2007

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A series of chiral imines derived from 1-amino-1-deoxyalditols such as d-glucamine, a rather unexplored raw material from the chiral pool, have been serendipitiously transformed into a novel family of N-acetyl-1,3-oxazolidines by means of an unexpected acetylation. The structure of these substances is supported by spectroscopic and crystallographic data. The acetylates also trigger a complex dynamic transformation, in which an initially configured trans oxazolidine converts into a more stable cis-configured derivative. Both isomers can also exist as rotational conformers (E,Z) as a consequence of the restricted rotation around the N-acetyl bond. The barriers to rotation have been determined by variable-temperature experiments. Overall, this transformation most likely involves the intermediacy of a chiral iminium ion, which has been documented in the synthesis of nitrogen heterocycles, thus explaining the experimental facts.

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