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Diastereoselective synthesis of functionalized spiro[cyclopropane-1,3′-indolines] and spiro[indoline-3,1′-cyclopropane-2′,3″-indolines]

Research paper by Wen-Jie Qi, Ying Han, Chao-Guo Yan

Indexed on: 14 Jun '16Published on: 11 Jun '16Published in: Tetrahedron



Abstract

In the presence of hexamethylphosphorous triamide, the reaction of isatin with arylidene pivaloylacetonitriles in dry methylene dichloride afforded functionalized spiro[cyclopropane-1,3′-indolines] in good yields and with high diastereoselectivity. Moreover, the similar reaction of isatins with isatylidene malononitriles predominately gave spiro[indoline-3,1′-cyclopropane-2′,3″-indolines] in very high yields with two indoline moieties in trans-configuration.

Graphical abstract 10.1016/j.tet.2016.06.020.jpg
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