2-Picoline catalyst-triggered [2 + 2 + 2] cycloaddition-type reaction of acetylenedicarboxylates, aldehydes and alkenes. Issue 33 (10th August 2018)

• Record Type: Journal Article
• Authors: Tateishi, Keiichiro; Noguchi, Keiichi; Saito, Akio
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 33(2018)
• Page Start: 5965
• Page End: 5968
• Publication Date: 2018-08-10
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob01774c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : 2-Picoline efficiently catalyzes the formation of α, β-enones from acetylenedicarboxylates and aldehydes in the presence of alkenes, thereby leading to pyrans with complete regioselectivities. This method is represented as a first example of catalytic and metal-free [2 + 2 + 2] cycloaddition of three different components. Abstract : 2-Picoline efficiently catalyzes the formation of α, β-enones from acetylenedicarboxylates and aldehydes in the presence of alkenes, thereby leading to pyrans in moderate to good yields with complete regioselectivities. This synthetic method of pyrans is represented as a first example of catalytic and direct [2 + 2 + 2] cycloaddition of three different components under the metal-free conditions.