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Org Lett. 2018 Oct 19;20(20):6403-6406. doi: 10.1021/acs.orglett.8b02701. Epub 2018 Oct 1.

Ming-Phos/Gold(I)-Catalyzed Diastereo- and Enantioselective Synthesis of Indolyl-Substituted Cyclopenta[ c]furans.

Author information

1
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering , East China Normal University , 3663 North Zhongshan Road , Shanghai 200062 , P. R. China.
2
Department of Obstetrics and Gynecology, Shanghai General Hospital , Shanghai Jiaotong University , 100 Haining Road , Shanghai 200080 , China.

Abstract

A highly enantioselective gold(I)-catalyzed intermolecular tandem cyclization/[3 + 2] cycloaddition of 2-(1-alkynyl)-2-alken-1-ones with 3-stylindoles was achieved by using Ming-Phos as a chiral ligand. A variety of chiral highly substituted cyclopenta[ c]furans were obtained in good yields (up to 99%) with excellent diastereoselectivities (>20:1) and enantioselectivities (up to 97% ee). The salient features of the present protocol include mild conditions, excellent yields, and high diastereo- and enantioselectivities, using readily available starting materials and a chiral ligand.

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