What question did this study set out to answer?

To develop a nickel-catalyzed regio- and stereoselective cyclization of functionalized oxanorbornenes with alkyl propiolates for synthesizing benzocoumarin derivatives.

April 1, 2001Angewandte Chemie

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 develop a nickel-catalyzed regio- and stereoselective cyclization of functionalized oxanorbornenes with alkyl propiolates for synthesizing benzocoumarin derivatives.
Coupled various substituted 7-oxabenzonorbornadienes with alkyl propiolates in a one-pot cyclization.
Used [NiBr2(dppe)] as the catalyst precursor alongside zinc powder in acetonitrile at 80 °C.
Obtained benzocoumarin derivatives in high chemical yields.
Achieved high regio- and stereoselectivity across diverse functional group substitutions on the oxanorbornene core.

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Implication

Experimental study demonstrates a nickel-catalyzed cyclization of oxanorbornenes with alkyl propiolates, highlighting an efficient route to synthesize stereoselective benzocoumarins.

Cite This Study

Rayabarapu et al. (2001) studied this question.

synapsesocial.com/papers/6a94cb77222f50f5880b173b https://doi.org/10.1002/1521-3757(20010401)113:7<1326::aid-ange1326>3.0.co;2-0

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Implication

Experimental study demonstrates a nickel-catalyzed cyclization of oxanorbornenes with alkyl propiolates, highlighting an efficient route to synthesize stereoselective 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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