Nucleophilic addition of regioselectively lithiated indoline with aldimines for the syntheses of 2- and 7-indolinyl methanamine derivatives |
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| Authors: | Liang ChengLi Liu Chuan LiHan Jia Dong WangYong-Jun Chen |
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| Institution: | Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China |
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| Abstract: | Indolines bearing different N-protecting groups (N-Tbf and N-Boc) were deprotonated regioselectively at C-2 (sp3 hybridized ortho-H) and C-7 (sp2 hybridized para-H) of the indoline ring, respectively. The generated organolithium intermediates reacted with aldimines to give the desired products in good yields with excellent anti-diastereoselectivities (>99:1). The produced N-Ts-(1-Tbf-indolin-2-yl)methanamine was facilely transformed to a fused heterocyclic compound. |
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| Keywords: | Indoline ortho-Lithiation para-Lithiation Imine Indolinyl methanamines |
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