Asymmetric conjugate addition–cyclization of cyclohexane-1, 2-dione with alkylidenemalononitriles using diaminomethylenemalononitrile organocatalyst. (11th May 2022)

• Record Type: Journal Article
• Authors: Matsushima, Yasuyuki; Iino, Yuta; Tsuruta, Yuka; Nakashima, Kosuke; Hirashima, Shin-ichi; Miura, Tsuyoshi
• Is Part Of: Tetrahedron letters. Volume 97(2022)
• Publication Date: 2022-05-11
• Subjects: Organocatalyst -- Asymmetric conjugate addition -- Cyclohexane-1, 2-dione -- Benzylidenemalononitrile -- Cyclization; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.153773
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A diaminomethylenemalononitrile organocatalyst efficiently promoted the asymmetric conjugate addition-cyclization of cyclohexane-1, 2-dione with benzylidenemalononitriles, resulting in the corresponding 2-amino-8-oxo-5, 6, 7, 8-tetrahydro-4 H -chromene-3-carbonitriles in high yields with excellent enantioselectivities (up to 90% ee). Use of the novel diaminomethylenemalononitrile organocatalyst made it possible to obtain the desired products with higher enantioselectivities compared with the previous reports.