Synthesis 2014; 46(16): 2161-2167
DOI: 10.1055/s-0033-1341204
special topic
© Georg Thieme Verlag Stuttgart · New York

Highly Diastereoselective Synthesis of Cyclopentenones via a One-Pot Gold Catalysis, Nazarov Cyclization and Alkylation Cascade

Authors

  • Meng-Qi Liu

    State Key Laboratory for Physical Chemistry of Solid Surfaces, The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China   Fax: +86(592)2185833   Email: longwuye@xmu.edu.cn
  • Ai-Hua Zhou

    State Key Laboratory for Physical Chemistry of Solid Surfaces, The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China   Fax: +86(592)2185833   Email: longwuye@xmu.edu.cn
  • Shuang Jiang

    State Key Laboratory for Physical Chemistry of Solid Surfaces, The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China   Fax: +86(592)2185833   Email: longwuye@xmu.edu.cn
  • Jia-Qi Wang

    State Key Laboratory for Physical Chemistry of Solid Surfaces, The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China   Fax: +86(592)2185833   Email: longwuye@xmu.edu.cn
  • Long-Wu Ye*

    State Key Laboratory for Physical Chemistry of Solid Surfaces, The Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China   Fax: +86(592)2185833   Email: longwuye@xmu.edu.cn
Further Information

Publication History

Received: 18 February 2014

Accepted: 21 March 2014

Publication Date:
09 April 2014 (online)


Graphical Abstract

Preview

Abstract

Starting from readily available propargylic carboxylates, three sequential transformations [gold-catalyzed tandem reaction, scandium(III) trifluoromethanesulfonate catalyzed Nazarov cyclization, alkylation reaction] in a one-pot process led to the formation of cyclopentenone derivatives in excellent diastereoselectivities and moderate to good overall yields.

Supporting Information