title: Diastereo- and enantioselective nitro-Mannich reaction of α-substituted nitroacetates to N-phosphoryl imines catalyzed by cinchona alkaloid thiourea organocatalysts.
abstract: The asymmetric nitro-Mannich reaction of N-phosphoryl imines with α-substituted nitroacetates was performed by using cinchona alkaloid thioureas as organocatalysts in toluene at -20 °C. The present method was highly tolerable to functionalized N-phosphoryl imines and provided a reliable synthetic route to obtain the corresponding β-nitro ethylphosphoramidates with adjacent quaternary and tertiary chiral centers in high yield (up to 86%) and high enantiostereoselectivity (up to 99% ee) and diastereoselectivity (up to 99 : 1, anti-selectivity).
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China.
authors.forename: Weidong
authors.initials: W
authors.lastname: Fan
authors.forename: Shasha
authors.initials: S
authors.lastname: Kong
authors.forename: Yan
authors.initials: Y
authors.lastname: Cai
authors.forename: Guiping
authors.initials: G
authors.lastname: Wu
authors.forename: Zhiwei
authors.initials: Z
authors.lastname: Miao
mesh_terms: D000085:Acetates / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
chemical_list: D000085:Acetates; D002930:Cinchona Alkaloids; D007097:Imines; C028257:nitroacetic acid; D013890:Thiourea