Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 17, Pages 9879-9889Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01282
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Funding
- National Natural Science Foundation of China [21702032, 21472022, 21772027]
- China Postdoctoral Science Foundation [2016M600287]
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An approach to access 1-substituted isoquinolones has been developed through the addition-cyclization of imines with Grignard reagents in the presence of 2,2'-dipyridyl. A number of substituted aromatic magnesium reagents were amenable to this process, and the desired products were obtained with excellent yields and outstanding diastereoselectivities (dr > 99:1). The utility of this convenient approach is demonstrated by the formal synthesis of (S)-cryptostyline II. Moreover, N-methylmorpholine (NMM) was found to be an effective additive for the formation of 3-substituted isoindolin-l-ones using one-pot addition-cyclization-deprotection of imine with Grignard reagents.
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