Diastereoselective arylation of L-proline derivatives at the 5-position

作者：Onomura Osamu^*; Kirira Peter G; Tanaka Toshimitsu; Tsukada Shinsuke; Matsumura Yoshihiro; Demizu Yosuke

来源：Tetrahedron, 2008, 64(32): 7498-7503.

DOI：10.1016/j.tet.2008.06.004

• diastereoselective
• organocatalysis
• asymmetric reduction of imines
• C(2)-symmetrical pyrrolidine
• proline derivative

Diastereoselective introduction of nucleophiles into L-proline derivatives at the 5-position was achieved with suitable selection of N-protecting group. N-Methoxycarbonylated or benzyloxycarbonylated L-proline derivatives reacted with arene to give cis-arylated products. On the other hand, N-benzoylated L-proline derivative preferentially gave trans-arylated product, which could be easily transformed into optically active C(2)-symmetrical pyrrolidine derivative. Such derivative 5 worked well as an organic activator in the asymmetric reduction of aromatic imines by Cl(3)SiH.

• 出版日期2008-8-4