Diastereoselective conjugate addition of organocuprates to N-[4-(Dibenzylaminobutenoyl)]oxazolidinone. Synthesis of chiral β-substituted γ-aminoacids. Issue 25 (20th June 2019)

• Record Type: Journal Article
• Authors: Assad, Salomón; Sabala, Rocío; Jiménez, Jacqueline; Sansinenea, Estibaliz; Ortiz, Aurelio
• Is Part Of: Tetrahedron letters. Volume 60:Issue 25(2019)
• Page Start: 1646
• Page End: 1648
• Publication Date: 2019-06-20
• Subjects: Asymmetric synthesis -- γ-Aminoacids -- Conjugate addition; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.05.035
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The first conjugate addition reaction of organocuprates to N -enoyl oxazolidinone. γ-Nitrogen atom is present into α, β-unsaturated system. The reaction gave syn -products in moderate yields and high diastereomeric ratios. Abstract: The first conjugate addition reaction of organocuprates to N -enoyl oxazolidinone where a γ-nitrogen atom is present into α, β-unsaturated system is described. The reaction gave syn -products in moderate yields and high diastereomeric ratios. The removal of chiral oxazolidinone moiety and N -deprotection of amino group furnished chiral β-substituted γ -amino acids.