A ruthenium-catalyzed ring opening-ring closing metathesis reaction serves as the key step in the stereoselective synthesis of a new enantiopure 2-substituted-4.5-dehydropiperidine skeleton, a valuable intermediate for the synthesis of piperidine alkaloids (such as halosaline) and of hydroxylated quinolizidines (such as (2R,9aR)-(+)-2-hydroxy-quinolizidine).
Concise Asymmetric Synthesis of (-)-Halosaline and (2R,9aR)-(+)-2-Hydroxy-Quinolizidine by Ruthenium-Catalyzed Ring-Rearrangement Metathesis / G. Lesma, S. Crippa, B. Danieli, D. Passarella, A. Sacchetti, A. Silvani, A. Virdis. - In: TETRAHEDRON. - ISSN 0040-4020. - 60:31(2004), pp. 6437-6442.
Concise Asymmetric Synthesis of (-)-Halosaline and (2R,9aR)-(+)-2-Hydroxy-Quinolizidine by Ruthenium-Catalyzed Ring-Rearrangement Metathesis
G. LesmaPrimo
;S. CrippaSecondo
;B. Danieli;D. Passarella;A. SilvaniPenultimo
;
2004
Abstract
A ruthenium-catalyzed ring opening-ring closing metathesis reaction serves as the key step in the stereoselective synthesis of a new enantiopure 2-substituted-4.5-dehydropiperidine skeleton, a valuable intermediate for the synthesis of piperidine alkaloids (such as halosaline) and of hydroxylated quinolizidines (such as (2R,9aR)-(+)-2-hydroxy-quinolizidine).
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