Allenl azide cycloaddtion chemistry. Photochemical initiation and cul mediation leads to improved regioselectivity

Ken S. Feldman; D. Keith Hester; Carlos Silva Lpez; Olalla Nieto Faza

doi:10.1021/ol800429j

Allenl azide cycloaddtion chemistry. Photochemical initiation and cul mediation leads to improved regioselectivity

Ken S. Feldman, D. Keith Hester, Carlos Silva Lpez, Olalla Nieto Faza

Chemistry

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

Irradiation of 2-(3-alkenyl)allenylphenyl azides in the presence of excess Cul 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.

Original language	English (US)
Pages (from-to)	1665-1668
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	8
DOIs	https://doi.org/10.1021/ol800429j
State	Published - Apr 17 2008

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol800429j

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abstract = "Irradiation of 2-(3-alkenyl)allenylphenyl azides in the presence of excess Cul 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.",

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AU - Feldman, Ken S.

AU - Hester, D. Keith

AU - Lpez, Carlos Silva

AU - Faza, Olalla Nieto

PY - 2008/4/17

Y1 - 2008/4/17

N2 - Irradiation of 2-(3-alkenyl)allenylphenyl azides in the presence of excess Cul 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.

AB - Irradiation of 2-(3-alkenyl)allenylphenyl azides in the presence of excess Cul 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.

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Allenl azide cycloaddtion chemistry. Photochemical initiation and cul mediation leads to improved regioselectivity

Abstract

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