Regio- and diastereoselective formation of some (η6-2-methylindoline)tricarbonylchromium(0) complex derivatives

被引:4
作者
Costa, MFD [1 ]
da Costa, MRG [1 ]
Curto, MJM [1 ]
机构
[1] Dept Tecnol Ind Quim, Inst Nacl Engn & Tecnol Ind, P-1649038 Lisbon, Portugal
关键词
indolines; arene complexes; asymmetric synthesis; chromium;
D O I
10.1016/S0022-328X(01)00694-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Complexation of 2-methylindoline 1 and its derivatives 2 and 3 with Cr(CO)(6) gave complexes 4-9. With the TIPS group attached to the nitrogen atom as in compound 3, the complexation was completely diastereoselective producing the endo complex 9. Treatment of the metallated complexes 8 and 9 with 2-halobenzoyl chlorides as electrophiles allowed for totally regioselective functionalisation at C(4), while the exo complex 6 was functionalised both at C(4) and C(7); with TMSCl and TIPSCl as electrophiles, the endo complex 9 also exhibited minor exo benzylic substitution to give 25 and 27. Oxidative decomplexation of the indoline complexes efficiently releases the free 4-substituted indolines. (C) 2001 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:233 / 242
页数:10
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