Organocatalytic regiospecific synthesis of 1H-indene-2-carbaldehyde derivatives: suppression of cycloolefin isomerisation by employing sterically demanding catalysts. Issue 6 (15th November 2016)

• Record Type: Journal Article
• Authors: Mao, Hui; Kim, Dong Wan; Shin, Hun Yi; Song, Choong Eui; Yang, Jung Woon
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 6(2017)
• Page Start: 1355
• Page End: 1362
• Publication Date: 2016-11-15
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob01918h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Extremely high regioselectivity (>99%) for indene-aldehyde products was achieved by using sterically demanding catalysts. Abstract : The regiospecific synthesis of 1 H -indene-2-carbaldehyde derivatives was achieved through transition-metal-free, reductive cyclisation of ortho -formyl trans -cinnamaldehydes with Hantzsch ester in the presence of an aminocatalyst. In particular, cycloolefin isomerisation of the resulting products could be inhibited efficiently by the introduction of a sterically demanding stereo-defined aminocatalyst.