Advanced Synthesis and Catalysis
Advanced Synthesis and Catalysis
5 years ago

Catalytic Asymmetric [4+1] Cyclization of ortho-Quinone Methides with 3-Chlorooxindoles

Catalytic Asymmetric [4+1] Cyclization of ortho-Quinone Methides with 3-Chlorooxindoles
Feng Shi, Yu-Qi Gu, Xiao-Li Jiang, Guang-Jian Mei, Si-Jia Liu
In this work, we established catalytic asymmetric [4+1] cyclization of ortho-quinone methides (o-QMs) with 3-chlorooxindoles and a catalytic asymmetric domino oxidation/[4+1] cyclization reaction of 2-alkylphenols with 3-chlorooxindoles, which constructed a spirooxindole-based 2,3-dihydrobenzofuran scaffold in good yield (up to 97%), with excellent diastereoselectivity (up to >95:5 dr) and high enantioselectivity (up to 99% ee). This work is not only the first highly enantioselective [4+1] cyclization of o-QMs but has also realized the first catalytic asymmetric domino [4+1] cyclization of o-QMs. In addition, both of the reactions provide efficient stereoselective methods for constructing spirooxindole-based 2,3-dihydrobenzofuran scaffolds with optical purity.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/adsc.201700487

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