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Chem Commun (Camb). 2016 Feb 7;52(11):2257-60. doi: 10.1039/c5cc08880a.

Gold-catalyzed construction of two adjacent quaternary stereocenters via sequential C-H functionalization and aldol annulation.

Author information

1
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, China. lliu@chem.ecnu.edu.cn jlzhang@chem.ecnu.edu.cn.
2
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, China. lliu@chem.ecnu.edu.cn jlzhang@chem.ecnu.edu.cn and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032, China.

Abstract

Herein, a novel and efficient gold-catalyzed intermolecular C(sp(2))-H functionalization (Friedel-Crafts alkylation) and aldol annulation strategy is presented. This cascade process allows the synthesis of a series of indanol and tetrahydronaphthalenol derivatives with two adjacent quaternary stereocenters. The attractive reaction features are the use of readily available starting materials, good diastereoselectivity, good functional-group tolerance and mild reaction conditions. Furthermore, preliminary results indicate that this transformation is amenable to enantioselectivitive synthesis with further chiral ligand screening and design.

PMID:
26725981
DOI:
10.1039/c5cc08880a

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