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Exploring cyclization strategies to access stemona alkaloids: subtle effects influencing reactivity in intramolecular Michael additions

Olivier, WJ, Babaahmadi, R, Lucas, N, Ariafard, A ORCID: 0000-0003-2383-6380, Bissember, AC ORCID: 0000-0001-5515-2878 and Smith, JA ORCID: 0000-0001-6313-3298 2021 , 'Exploring cyclization strategies to access stemona alkaloids: subtle effects influencing reactivity in intramolecular Michael additions' , Organic Letters, vol. 23, no. 21 , pp. 8494-8498 , doi: 10.1021/acs.orglett.1c03205.

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Abstract

This report investigates the fundamental basis for rather surprising patterns of reactivity in Brønsted acid-mediated cyclizations of pyrrole substrates bearing pendant Michael acceptors that were identified during syntheses of Stemona alkaloids. Integrated experimental and theoretical studies reveal the profound influence that substituent effects have on the viability of these transformations. Additionally, we identify that electronic effects, in addition to barrier-lowering secondary orbital interactions within transition states, account for the exclusive preference for 7-endo-trig cyclizations over 6-exo-trig cyclizations.

Item Type: Article
Authors/Creators:Olivier, WJ and Babaahmadi, R and Lucas, N and Ariafard, A and Bissember, AC and Smith, JA
Keywords: stemona alkaloids, pyrrole, Michael addition, DFT
Journal or Publication Title: Organic Letters
Publisher: Amer Chemical Soc
ISSN: 1523-7060
DOI / ID Number: 10.1021/acs.orglett.1c03205
Copyright Information:

Copyright 2021 American Chemical Society

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