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Org Lett. 2017 May 19;19(10):2526-2529. doi: 10.1021/acs.orglett.7b00804. Epub 2017 May 05.

Synthesis of Spiroketals by Synergistic Gold and Scandium Catalysis.

Organic letters

Man Liang, Shuai Zhang, Jiong Jia, Chen-Ho Tung, Jianwu Wang, Zhenghu Xu

Affiliations

  1. Key Laboratory for Colloid and Interface Chemistry of Education Ministry, School of Chemistry and Chemical Engineering, Shandong University , Jinan 250100, China.
  2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , Shanghai 200032, China.

PMID: 28474897 DOI: 10.1021/acs.orglett.7b00804

Abstract

An ultrafast synthesis of spiroketals by synergistic gold(I) and Sc(III) catalysis has been reported. Diverse 5,6-benzannulated spiroketals were rapidly constructed by the diastereoselective [4 + 2] cycloaddition between gold-generated enol ether and Sc(III)-catalyzed o-quinone methide intermediates. Ultrafast reaction rate, ambient reaction temperature, general scope, high yields, excellent diastereoselectivity, and good scalability are attractive features of this method.

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