What question did this study set out to answer?

To establish an efficient, highly regio- and stereoselective catalytic pathway for the synthesis of benzocoumarin derivatives from oxanorbornenes and alkyl propiolates.

April 1, 2001Angewandte Chemie International Edition

Nickel-Catalyzed Highly Regio- and Stereoselective Cyclization of Oxanorbornenes with Alkyl Propiolates: A Novel Method for the Synthesis of Benzocoumarin Derivatives

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To establish an efficient, highly regio- and stereoselective catalytic pathway for the synthesis of benzocoumarin derivatives from oxanorbornenes and alkyl propiolates.
Coupled 7-oxabenzonorbornadienes containing various substituents with alkyl propiolates in a one-pot reaction format.
Conducted reactions at 80°C in acetonitrile using [NiBr2(dppe)] as the catalyst precursor in combination with zinc powder reductant.
The one-pot catalytic protocol afforded functionalized benzocoumarin derivatives in consistently good chemical yields.
The cyclization proceeded with high levels of regio- and stereoselectivity across varied oxabicyclic substrate substitutions.

Authors

DRDinesh Kumar RayabarapuUniversity of Kansas TSThota SambaiahAstraZeneca (United States)CCChien‐Hong ChengNational Sun Yat-sen University

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Implication

Experimental study demonstrates nickel-catalyzed cyclization of oxanorbornenes with propiolates, indicating an efficient selective route to produce substituted benzocoumarins.

Cite This Study

Rayabarapu et al. (2001) studied this question.

synapsesocial.com/papers/6a94c97a9b63464d9ec097bc https://doi.org/10.1002/1521-3773(20010401)40:7<1286::aid-anie1286>3.0.co;2-i

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Implication

Experimental study demonstrates nickel-catalyzed cyclization of oxanorbornenes with propiolates, indicating an efficient selective route to produce substituted benzocoumarins.

Nickel-Catalyzed Highly Regio- and Stereoselective Cyclization of Oxanorbornenes with Alkyl Propiolates: A Novel Method for the Synthesis of Benzocoumarin Derivatives

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Discussion

Implication

Cite This Study

Nickel-Catalyzed Highly Regio- and Stereoselective Cyclization of Oxanorbornenes with Alkyl Propiolates: A Novel Method for the Synthesis of Benzocoumarin Derivatives

Key Points

Discussion

Implication

Cite This Study

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