Pure Appl. Chem., 2005, Vol. 77, No. 12, pp. 2053-2059
http://dx.doi.org/10.1351/pac200577122053
Dual enantioselective control by heterocycles of (S)-indoline derivatives
Abstract:
Diastereo-and enantioselective pinacol coupling reactions of chiral α-ketoamides mediated by samarium diiodide afforded extremely high diastereoselectivities. Enantiopure (S,S)- or (R,R)-2,3-dialkyltartaric acid and derivatives can be synthesized. Diels-Alder cycloadditions of S-indoline chiral acrylamides with cyclopentadiene in the presence of Lewis acids proceed with high diastereofacial selectivity, giving either endo-R or endo-S products depending on Lewis acid and the structures of chiral dienophiles.
Keywords
Enantioselective; pinacol coupling; samarium diiodide; S-indoline; α-ketoamides.