Diastereoselective conjugate addition of organocuprates to chiral N-enoyl oxazolidinethiones.
Addition of organocuprates, generated in situ using an excess of a 1:2 mixture of CuI·DMS and Grignard reagent, to N-enoyl oxazolidinethiones in the presence of excess TMSI gave preferentially the anti diastereomer where the addition took place when the conformation of the substrate was syn-s-cis. The reaction was investigated with indene-based and three different phenyl glycine derived oxazolidinethiones.
Sabala
Rocío
R
Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Pue. 72570, Mexico.
Hernández-García
Luis
L
Ortiz
Aurelio
A
Romero
Moisés
M
Olivo
Horacio F
HF
D003300:Copper / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010080:Oxazoles / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013871:Thiones / Q000138:chemical synthesis*
D009942:Organometallic Compounds; D010080:Oxazoles; D013871:Thiones; D003300:Copper