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

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

J Org Chem. 2018 Sep 7;83(17):9879-9889.

PMID: 29952568

Abstract:

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-1-ones using one-pot addition-cyclization-deprotection of imine with Grignard reagents.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP444315188	PSS-Vinyl-Heptaisobutyl substituted		444315-18-8	Price

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