Highly enantioselective and diastereoselective conjugate addition of 5H-oxazol-4-ones to 2-chloroacrylonitrile catalyzed by chiral guanidines. Issue 36 (2nd September 2015)

• Record Type: Journal Article
• Authors: Misaki, Tomonori; Choi, Na-Rae; Morita, Akane; Sugimura, Takashi
• Is Part Of: Tetrahedron letters. Volume 56:Issue 36(2015)
• Page Start: 5063
• Page End: 5066
• Publication Date: 2015-09-02
• Subjects: Organocatalysis -- Conjugate addition -- 5H-Oxazol-4-one -- Chiral guanidine -- Quaternary carbon center; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.07.063
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The chiral guanidine-catalyzed conjugate addition of 5 H -oxazol-4-ones to 2-chloroacrylonitrile was developed with high enantiomeric and diastereomeric control. Introduction of an electron-donating 4-methoxyphenyl group as an aromatic substituent (Ar) on 5 H -oxazol-4-one was suitable for inhibiting undesirable cyclization and achieving high stereoselectivity in this conjugate addition. The derivatization of an obtained product was also performed to afford a chiral α-siloxyimide, which was subsequently converted to the corresponding α-siloxy-γ-lactam in a few steps.