Post-Ugi Cascade Transformations for Accessing Diverse Chromenopyrrole Collections

Vunnam Srinivasulu, Scott Mc N. Sieburth, Raafat El-Awady, Noor M. Kariem, Hamadeh Tarazi, Matthew O'Connor, Taleb H. Al-Tel

Research output: Contribution to journalArticle

Abstract

Employing a build/couple/pair strategy, a serendipitous one-pot protocol for the diastereoselective construction of diverse collections of chromenopyrroles is described. This methodology features an unprecedented five-step cascade including azomethine ylide generation followed by in situ intramolecular [3 + 2]-cycloaddition. Furthermore, this protocol was extended to access enantiopure chromenopyrroles using amino acids as chiral auxiliary. Moreover, postpairing reactions were employed to increase the diversity and complexity of our pilot compound collections.

Original languageEnglish (US)
Pages (from-to)836-839
Number of pages4
JournalOrganic Letters
Volume20
Issue number3
DOIs
StatePublished - Feb 2 2018

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Cycloaddition
Cycloaddition Reaction
cascades
Amino Acids
cycloaddition
amino acids
methodology
azomethine

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Srinivasulu, V., Sieburth, S. M. N., El-Awady, R., Kariem, N. M., Tarazi, H., O'Connor, M., & Al-Tel, T. H. (2018). Post-Ugi Cascade Transformations for Accessing Diverse Chromenopyrrole Collections. Organic Letters, 20(3), 836-839. https://doi.org/10.1021/acs.orglett.7b03986

Post-Ugi Cascade Transformations for Accessing Diverse Chromenopyrrole Collections. / Srinivasulu, Vunnam; Sieburth, Scott Mc N.; El-Awady, Raafat; Kariem, Noor M.; Tarazi, Hamadeh; O'Connor, Matthew; Al-Tel, Taleb H.

In: Organic Letters, Vol. 20, No. 3, 02.02.2018, p. 836-839.

Research output: Contribution to journalArticle

Srinivasulu, V, Sieburth, SMN, El-Awady, R, Kariem, NM, Tarazi, H, O'Connor, M & Al-Tel, TH 2018, 'Post-Ugi Cascade Transformations for Accessing Diverse Chromenopyrrole Collections', Organic Letters, vol. 20, no. 3, pp. 836-839. https://doi.org/10.1021/acs.orglett.7b03986
Srinivasulu, Vunnam ; Sieburth, Scott Mc N. ; El-Awady, Raafat ; Kariem, Noor M. ; Tarazi, Hamadeh ; O'Connor, Matthew ; Al-Tel, Taleb H. / Post-Ugi Cascade Transformations for Accessing Diverse Chromenopyrrole Collections. In: Organic Letters. 2018 ; Vol. 20, No. 3. pp. 836-839.
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