Abstract
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.
Original language | English |
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Pages (from-to) | 3945-3948 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 52 |
Issue number | 30 |
DOIs | |
State | Published - 27 Jul 2011 |
Keywords
- Desulfurisation
- Enantioselective synthesis
- Progesterone receptor antagonist
- Radical cyclization