The Castagnoli-Cushman reaction in a three-component format. Issue 26 (27th June 2018)

• Record Type: Journal Article
• Authors: Chupakhin, Evgeny; Dar'in, Dmitry; Krasavin, Mikhail
• Is Part Of: Tetrahedron letters. Volume 59:Issue 26(2018)
• Page Start: 2595
• Page End: 2599
• Publication Date: 2018-06-27
• Subjects: Homophthalic acid -- Schiff base -- Cyclodehydration -- Azeotropic water removal -- The Castagnoli-Cushman reaction -- Diastereoselectivity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.05.066
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The Castagnoli-Cushman reaction was realized in a truly three-component format. Dehydration of a mixture of homophthalic acid with amine and aldehyde is employed. The method requires no dehydrative agent and uses azeotropic removal of water. The method is specifically suitable for combinatorial array development. The reaction is stereoselective over the scaffold and periphery stereocenters. Abstract: The first example of the Castagnoli-Cushman reaction of homophthalic acid with an amine and an aldehyde conducted in a three-component format is reported. This new protocol employs no dehydrating agents and, unlike the traditional Castagnoli-Cushman reaction of homophthalic anhydride, allows simultaneous mixing of all three reagents and provides good to excellent yields of trans -configured tetrahydroisoquinolonic acids.