DBU-mediated diastereoselective aldol-type cyanomethylation of isatins

TitleDBU-mediated diastereoselective aldol-type cyanomethylation of isatins
Publication TypeJournal Article
Year of Publication2017
AuthorsRao, VUBhaskar, Kumar, K, Das, T, Vanka, K
JournalJournal of Organic Chemistry
Date PublishedAPR
Type of ArticleArticle
AbstractAn efficient, metal-free approach to 3-substituted 3-hydroxybxindole by DBU-mediated highly diastereoselective addition of aryl acetonitrile to N-protected isatin under mild conditions has been developed. The reaction proceeds smoothly to produce respective cyanomethylated adducts in good yield and excellent diastereoselectivity. Further transformation of the cyanide group allowed the synthesis of an advance intermediate of corresponding (+/-) CPC analogue. The mechanistic insight :toward the aldol-type cyanomethylation, of N-tritylisatin with benzyl cyanide was obtained by DFT calculations.
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)4.785
Divison category: 
Physical and Materials Chemistry

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