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
相关论文
共 56 条
[51]  
TOCQUER MCS, 1992, B SOC CHIM FR, V129, P121
[52]   ARENE-METAL COMPLEXES .4. BASE-CATALYZED STEREOSELECTIVE HYDROGEN-DEUTERIUM EXCHANGE OF BENZYLIC PROTONS OF TRICARBONYLCHROMIUM(0)-COMPLEXED ALKYLBENZENES [J].
TRAHANOVSKY, WS ;
CARD, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (08) :2897-+
[53]  
Uemura M., 1991, ADV METAL ORGANIC CH, V2, P195
[54]   Metal-catalyzed reaction of indoline diazoamides possessing a C-2 CH(2)X substituent: Site-selectivity, diastereoselectivity, and chemoselectivity [J].
Wee, AGH ;
Slobodian, J .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) :2897-2900
[55]   A synthesis of functionalized indoline 2,2-biscarboxylates [J].
Wright, SW ;
Dow, RL ;
McClure, LD ;
Hageman, DL .
TETRAHEDRON LETTERS, 1996, 37 (39) :6965-6968
[56]   A versatile synthesis of 3-substituted indolines and indoles [J].
Zhang, DW ;
Liebeskind, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) :2594-2595