J. Wilken, Michael Kossenjans, W. Saak
Mar 1, 1997
Citations
0
Influential Citations
21
Citations
Journal
Liebigs Annalen
Abstract
New, chiral bicyclic 3-hydroxypiperidines (4S)-2a–e are synthesized from the β-amino alcohols (3R)-1a–e. In an one-step reaction (4S)-2a–e are obtained by a high diastereoselective ring expansion (dr ⩾ 95:5). As well, the amino alcohol (3S)-1a leads to the corresponding rearranged epimer bicyclic piperidine derivative (4R)-2a (dr ⩾ 95:5). Thus, it is possible to clarify the influence of the three stereogenic centers of the parent compound regarding the diastereoselectivity of the ring expansion. After oxidation of the tert-amino sec-alcohol (4S)-2a to the corresponding α-amino ketone 4, new 3-hydroxypiperidines (4Ξ)-5a, b12 and (4RS)-6 are obtained by a diastereoselective Grignard addition. Furthermore, the achiral and the chiral reduction of 4 to the β-amino alcohols (4S)-2a and (4R)-2a is described. These are further examples of the utilization of industrial waste material (all-R)-2-azabicyclo[3.3.0]octane-3-carboxylic acid (all-R)-3.