Volume 59, Issue 6 pp. 2220-2224
Communication

Asymmetric Synthesis of a Fused Tricyclic Hydronaphthofuran Scaffold by Desymmetric [2+2+2] Cycloaddition

Qi Teng

Qi Teng

Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China

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Wenxiu Mao

Wenxiu Mao

Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China

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Dong Chen

Dong Chen

Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China

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Zhen Wang

Zhen Wang

Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China

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Prof. Dr. Chen-Ho Tung

Prof. Dr. Chen-Ho Tung

Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China

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Prof. Dr. Zhenghu Xu

Corresponding Author

Prof. Dr. Zhenghu Xu

Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 China

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 China

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First published: 20 November 2019
Citations: 53

Dedicated to Professor Li-Xin Dai on the occasion of his 95th birthday

Graphical Abstract

A rhodium(I)-BINAP-catalyzed [2+2+2] cycloaddition of enynes with alkynes has been developed. Diverse fused tricyclic hydronaphthofuran scaffolds with three consecutive stereogenic centers were constructed in one step from easily available materials with excellent chemo-, regio-, diastereo-, and enantioselectivity. Notable features of these reactions include 100 % atom economy, very broad scope, and mild reaction conditions.

Abstract

A rhodium(I)-BINAP-catalyzed highly enantioselective [2+2+2] cycloaddition of enynes with alkynes has been developed. Diverse fused tricyclic hydronaphthofuran scaffolds with three consecutive stereogenic centers were constructed in one step from easily available materials with excellent chemo-, regio-, diastereo-, and enantioselectivity. Notable features of these reactions include 100 % atom economy, very broad scope, and mild reaction conditions.

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