Synthesis of functionalised piperidines through a [3+3] cycloaddition strategy

Citation
Sj. Hedley et al., Synthesis of functionalised piperidines through a [3+3] cycloaddition strategy, SYNLETT, (10), 2001, pp. 1596-1598
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
10
Year of publication
2001
Pages
1596 - 1598
Database
ISI
SICI code
0936-5214(200110):10<1596:SOFPTA>2.0.ZU;2-R
Abstract
A novel approach to functionalised piperidines is described through a [3+3] cycloaddition reaction of aziridines with Pd-trimethylenemethane complexes . Importantly, the employment of enantiomerically pure aziridines (prepared in three steps from the appropriate amino acids) allows the corresponding piperidines to be furnished in enantiomerically pure form. Additionally, th e application of this technique in the total synthesis of (-)-pseudoconhydr ine is described.