Allenes and Transition Metals: a Diverging Approach to Heterocycles

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2004 Jun 18

PMID 15200331

Citations 16

Authors

Kay M Brummond

Branko Mitasev

Affiliations

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Abstract

[reaction: see text] An alkynyl allene has been converted to heterocycles possessing an alpha-alkylidene cyclopentenone, a 4-alkylidene cyclopentenone, or a cross-conjugated triene. Thus, a common intermediate has been converted to three structurally unique compounds by changing only the reaction conditions and, therefore, controlling various reaction pathways.

Citing Articles

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Deng X, Shi L, Lan J, Guan Y, Zhang X, Lv H Nat Commun. 2019; 10(1):949.

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Skeletal and Appendage Diversity as Design Elements in the Synthesis of a Discovery Library of Nonaromatic Polycyclic 5-Iminooxazolidin-2-ones, Hydantoins, and Acylureas.

Werner S, Turner D, Chambers P, Brummond K Tetrahedron. 2017; 64(29):6997-7007.

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Computational Insight Concerning Catalytic Decision Points of the Transition Metal Catalyzed [2 + 2 + 1] Reaction of Allenes.

Bayden A, Brummond K, Jordan K Organometallics. 2015; 25(22):5204-5206.

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Reactivity and chemoselectivity of allenes in Rh(I)-catalyzed intermolecular (5 + 2) cycloadditions with vinylcyclopropanes: allene-mediated rhodacycle formation can poison Rh(I)-catalyzed cycloadditions.

Hong X, Stevens M, Liu P, Wender P, Houk K J Am Chem Soc. 2014; 136(49):17273-83.

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Rh(I)-catalyzed Pauson-Khand-type cycloaddition reaction of ene-vinylidenecyclopropanes with carbon monoxide (CO).

Yuan W, Dong X, Shi M, McDowell P, Li G Org Lett. 2012; 14(21):5582-5.

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