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Asymmetric Synthesis of Trisubstituted Oxazolidinones by the Thiourea-Catalyzed Aldol Reaction of 2‑Isocyanatomalonate Diester

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journal contribution
posted on 19.09.2014 by Shota Sakamoto, Naoya Kazumi, Yusuke Kobayashi, Chihiro Tsukano, Yoshiji Takemoto
A new method has been developed for the synthesis of chiral 4-carboxyl oxazolidinones by the catalytic asymmetric aldol reaction of an isocyanatomalonate diester with an aldehyde in the presence of a thiourea catalyst. The resulting chiral 4-carboxyl oxazolidinones are the equivalent of β-hydroxy-α-amino acids bearing a tri- or tetrasubstituted carbon center at their α position. With this in mind, this procedure was successfully applied to the first total synthesis of mycestericin C, which was completed in 12 steps and represents one of the shortest reported sequences for the construction of natural products of this type.