Regio- and diastereoselective formation of some (η 6-2-methylindoline)tricarbonylchromium(0) complex derivatives

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-...

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Published inJournal of organometallic chemistry Vol. 626; no. 1; pp. 233 - 242
Main Authors Costa, M.Filomena D, da Costa, M.Rute G, Marcelo Curto, M.J
Format Journal Article
LanguageEnglish
Published Elsevier B.V 30.04.2001
Subjects
Arene complexes
Asymmetric synthesis
Chromium
Indolines
Chromium
Arene complexes
Asymmetric synthesis
Indolines
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Summary: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.
ISSN:0022-328X
1872-8561
DOI:10.1016/S0022-328X(01)00694-5