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
Volume82
Issue8
Pagination4489-4496
Date PublishedAPR
Type of ArticleArticle
Abstract

An 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.

DOI10.1021/acs.joc.7b00512
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

4.785

Divison category: 
Physical and Materials Chemistry