ISSN:
0947-3440
Keywords:
Amino alcohols
;
Bicyclic pyrrolidine and piperidine derivatives
;
Diastereoselective ring expansion
;
Chiral auxiliaries
;
Waste prevention
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970319
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