Direct Synthesis of Enolizable N-Sulfonyl Ketimines Under Microwave Irradiation

• Published in: European Journal of Organic Chemistry Vol. 2016; no. 7; pp. 1247 - 1250
• Main Authors: Pablo Ortiz, Collados, Juan F., Harutyunyan, Syuzanna R.
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.03.2016; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Chemistry; Chemistry, Organic; Condensation reactions; Imines; Ketimines; Microwave chemistry; Physical Sciences; Science & Technology; ALDIMINES; HYDROGENATION; Ketimines; TRIMETHYLENEMETHANE; Microwave chemistry; ENANTIOSELECTIVE CONSTRUCTION; Condensation reactions; Imines; PYRROLIDINES; ASYMMETRIC 3+2 CYCLOADDITION; EFFICIENT; STRECKER REACTION; SOLVENT-FREE SYNTHESIS
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201600022

N‐sulfonyl imines are widely used as substrates for a range of transformations. Access to N‐sulfonyl aldimines is straightforward through direct condensation between the parent aldehyde and the sulfonamide. However, this approach is not efficient for the synthesis of enolizable N‐sulfonyl ketimines. Herein we report a rapid and facile methodology for obtaining these products using microwave irradiation. Contrary to N‐sulfonyl aldimines, enolizable N‐sulfonyl ketimines cannot be efficiently synthesized by direct condensation between the parent carbonyl compound and the sulfonamide. Therefore, multi‐step procedures have to be used. We have developed a rapid and facile methodology for obtaining enolizable N‐sulfonyl ketimines in one step from commercially available reagents using microwave irradiation.