American Chemical Society
ol101687e_si_001.pdf (230.62 kB)

Diastereoselective Conjugate Addition of Organocuprates to Chiral N-Enoyl Oxazolidinethiones

Download (230.62 kB)
journal contribution
posted on 2010-10-01, 00:00 authored by Rocío Sabala, Luis Hernández-García, Aurelio Ortiz, Moisés Romero, Horacio F. Olivo
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.