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Approach to Chiral 1-Substituted Isoquinolone and 3-Substituted Isoindolin-1-one by Addition-Cyclization Process

Wen Zhou, Yan-Xue Zhang, Xiao-Di Nie, Chang-Mei Si*, Xun Sun, Bang-Guo Wei*

*Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, The People's Republic of China, Email:,

W. Zhou, Y.-X. Zhang, X.-D. Nie, C.-M. Si, X. Sun, G.-G. Wei, J. Org. Chem., 2018, 83, 9879-9889.

DOI: 10.1021/acs.joc.8b01282

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An addition-cyclization of α-chiral imines with substituted aromatic Grignard reagents in the presence of 2,2'-bipyridine provides isoquinolone products with excellent yields and outstanding diastereoselectivities. Moreover, N-methylmorpholine (NMM) was found to be an effective additive for the formation of 3-substituted isoindolin-1-ones using a one-pot addition-cyclization-deprotection sequence.

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Key Words

benzo-fused N-heterocycles

ID: J42-Y2018