1, 4-addition reaction of 5H-oxazol-4-ones to vinyl ketones catalyzed by chiral guanidines. Issue 1 (1st January 2015)

• Record Type: Journal Article
• Authors: Morita, Akane; Misaki, Tomonori; Sugimura, Takashi
• Is Part Of: Tetrahedron letters. Volume 56:Issue 1(2015)
• Page Start: 264
• Page End: 267
• Publication Date: 2015-01-01
• Subjects: Organocatalysis -- 1, 4-addition -- 5H-Oxazol-4-one -- Chiral guanidine -- Quaternary carbon center; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2014.11.079
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: In this Letter, a chiral guanidine-catalyzed 1, 4-addition reaction of 5 H -oxazol-4-ones to vinyl ketones is described. The 1, 4-addition reaction proceeded with a high enantioselectivity using 5 H -oxazol-4-ones, substituted with a 3-chloro-5-methylphenyl group, as pronucleophiles and a newly developed chiral guanidine as a catalyst. The optimized reaction conditions were also effective in achieving excellent enantioselectivity in the 1, 6-addition to dienones. Subsequent solvolysis of the 1, 4-addition adduct yielded the corresponding α-hydroxy-5-oxocarboxylates.