Allenyl Azide Cycloaddition Chemistry. Photochemical Initiation and CuI Mediation Leads to Improved Regioselectivity

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2008 Mar 19

PMID 18345683

Citations 6

Authors

Ken S Feldman

D Keith Hester 2nd

Carlos Silva Lopez

Olalla Nieto Faza

Affiliations

Soon will be listed here.

Abstract

Irradiation of 2-(3-alkenyl)allenylphenyl azides in the presence of excess CuI furnished functionalized 2,3-cyclopentenylindoles in good yield with only trace amounts of competitive C-N-bonded regioisomeric products. These results represent a significant departure from the modest-to-nonexistent regioselectivity that attended thermal cyclization of these allenyl azide substrates.

Citing Articles

Understanding the 1,3-Dipolar Cycloadditions of Allenes.

Yu S, Vermeeren P, van Dommelen K, Bickelhaupt F, Hamlin T Chemistry. 2020; 26(50):11529-11539.

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Nazarov cyclization of 1,4-pentadien-3-ols: preparation of cyclopenta[b]indoles and spiro[indene-1,4'-quinoline]s.

Wang Z, Xu X, Gu Z, Feng W, Qian H, Li Z Chem Commun (Camb). 2016; 52(13):2811-4.

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Synthesis studies on the Melodinus alkaloid meloscine.

Feldman K, Antoline J Tetrahedron. 2013; 69(5):1434-1445.

PMID: 23316092 PMC: 3539727. DOI: 10.1016/j.tet.2012.12.032.

Cyclization Cascade of Allenyl Azides: Synergy Between Theory and Experiment.

Nieto Faza O, Feldman K, Lopez C Curr Org Chem. 2012; 14(15):1646-1657.

PMID: 22347808 PMC: 3280692. DOI: 10.2174/138527210793563305.

Allenyl azide cycloaddition chemistry: application to the total synthesis of (±)-meloscine.

Feldman K, Antoline J Org Lett. 2012; 14(3):934-7.

PMID: 22242696 PMC: 3272129. DOI: 10.1021/ol203463n.

References

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