Abstract
The alkylation of indoles by aziridinium ions generated in situ from β-amino chlorides was explored. The outcome of this reaction strongly relied on the substitution pattern of the starting β-amino chloride and requires silver tetrafluoroborate activation to proceed in reasonable yield. Ephedrine- and pseudoephedrine-derived N-cyanomethyl-β-amino chlorides afforded the corresponding tryptamines in a regio- and stereoselective manner and subsequent silver(I)-promoted Pictet–Spengler reactions produced 4-phenyl substituted THBCs in good yields. Unexpected epimerization at C-3 was found in these reactions, producing trans-3,4-disubstituted THBCs stereoselectively.
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.
