Enantioselective synthesis of (7R,8R,8aR)- and (7S,8S,8aS)-7-hydroxy-8-indolizidinemethanol by 1,3-dipolar cycloaddition of 1-pyrroline N-oxide to chiral pentenoates

Authors
Cordero, FM Faggi, C De Sarlo, F Brandi, A
Citation
Fm. Cordero et al., Enantioselective synthesis of (7R,8R,8aR)- and (7S,8S,8aS)-7-hydroxy-8-indolizidinemethanol by 1,3-dipolar cycloaddition of 1-pyrroline N-oxide to chiral pentenoates, EUR J ORG C, (21), 2000, pp. 3595-3600
Citations number
69
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
21
Year of publication
2000
Pages
3595 - 3600
Database
ISI
SICI code
1434-193X(200011):21<3595:ESO(A(>2.0.ZU;2-K
Abstract
The 1,3-dipolar cycloadditions of pyrroline N-oxide (1) with (1R,2S)-trans- 2-phenylcyclohexyl- and with (1R,2S,5R)-8-phenylmenthyl-pent-2-enoates (9 a nd 10) proceed with op-posite diastereoselectivities. The two enantiomers o f a new dihydroxyindolizidine, (+)-6 and (-)-6, were synthesized using 4 an d 5, respectively, as the chiral auxiliary.