Abstract
The intramolecular aminomercuration of γ-alkenylamines 1a, 1b and 4 was shown to afford the 5-endo-trig cyclized product exclusively in good yield. The utility of pyrrolidine derivatives thus obtained from D-glucose derived γ-alkenylamines 1a and 1b was demonstrated in the synthesis of 1-deoxycastanospermine (3a) and 1-deoxy-8a-epi-castanospermine (3b).
Highlights
The pyrrolidine ring skeleton constitutes an important molecular backbone for a number of heterocyclic compounds
In case of γ-alkenylamines, only a single report is known on the mercury (II) mediated 5-endo-trig cyclization, leading to the formation of pyrrolidine ring, while the 4-exo-trig product is not obtained due to the ring strain involved in the four membered ring system [1d, 3]
In order to know whether the differentially substituted γ-alkenylamines obey the usual Baldwin’s ring closure rule or not [10], we have investigated the model reaction with α-phenyl-substituted-γalkenylamine 4
Summary
The pyrrolidine ring skeleton constitutes an important molecular backbone for a number of heterocyclic compounds.
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
