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

• DOI: 10.1002/adsc.201700487
• Publication Date: 2017-06-01T02:26:40Z
• Authors: Xiao‐Li Jiang; Si‐Jia Liu; Yu‐Qi Gu; Guang‐Jian Mei; Feng Shi
• Keywords: Domino

Abstract In this work, we established catalytic asymmetric [4+1] cyclization of ortho ‐quinone methides ( o ‐QMs) with 3‐chlorooxindoles and a domino oxidation/[4+1] reaction 2‐alkylphenols 3‐chlorooxindoles, which constructed spirooxindole‐based 2,3‐dihydrobenzofuran scaffold in good yield (up to 97%), excellent diastereoselectivity >95:5 dr ) high enantioselectivity 99% ee ). This work is not only the first highly enantioselective ‐QMs but has also realized ‐QMs. addition, both reactions provide efficient stereoselective methods for constructing scaffolds optical purity. magnified image