A convenient enantioselective synthesis of 3-asymmetrically substituted oxindoles as progesterone receptor antagonists

作者：Alluri S; Feng H; Livings M; Samp L; Biswas D; Lam T W; Lobkovsky E; Ganguly A K^*

来源：Tetrahedron Letters, 2011, 52(30): 3945-3948.

DOI：10.1016/j.tetlet.2011.05.120

• Radical cyclization
• Desulfurisation
• Enantioselective synthesis
• Progesterone receptor antagonist

A convenient enantioselective synthesis of 3-asymmetrically substituted oxindoles is reported. Compound (2) prepared by radical cyclisation of (1) was used for the synthesis of racemic and enantiomerically pure 3-asymmetrically substituted oxindoles. Desulfurisation of (2) using Raney Ni yielded the racemate (5). Addition of (S)-1-phenylethanol to compound (2) yielded the diastereoisomer (21) the structure of which was determined using X-ray crystallography. Using a sequence of steps (21) was converted to the enantiomer (8). The enantiomer (9) was similarly prepared from (2) using (R)-1-phenylethanol.

• 出版日期2011-7-27