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EnglishA practical catalytic approach to the synthesis of 4-substituted 1,2,3,4-tetrahydro-beta-carbolines (THBCs, 1) and 1,2,3,9-tetrahydropyrano[3,4-b] indoles ( 2) via InBr3-catalyzed intramolecular Friedel - Crafts ( F - C) cyclization is described. The use of cross-metathesis reaction represents a direct route to the cyclization precursors and the use of InBr3 ( 5 mol%) allowed polycyclic indole compounds to be isolated in high yields under mild reaction conditions (rt, DCM, minutes). Finally, efforts toward the development of a stereocontrolled version of the present cyclization are presented, highlighting [salenAlCl] and bimetallic [(salenAlCl)(2) - InBr3] system as promising chiral Lewis acids (ee up to 60%).
| Titolo: | A practical synthetic route to functionalized THBCs and oxygenated analogues via intramolecular Friedel-Crafts reactions |
| Autori: | |
| Data di pubblicazione: | 2006 |
| Rivista: | |
| Abstract: | A practical catalytic approach to the synthesis of 4-substituted 1,2,3,4-tetrahydro-beta-carbolines (THBCs, 1) and 1,2,3,9-tetrahydropyrano[3,4-b] indoles ( 2) via InBr3-catalyzed intramolecular Friedel - Crafts ( F - C) cyclization is described. The use of cross-metathesis reaction represents a direct route to the cyclization precursors and the use of InBr3 ( 5 mol%) allowed polycyclic indole compounds to be isolated in high yields under mild reaction conditions (rt, DCM, minutes). Finally, efforts toward the development of a stereocontrolled version of the present cyclization are presented, highlighting [salenAlCl] and bimetallic [(salenAlCl)(2) - InBr3] system as promising chiral Lewis acids (ee up to 60%). |
| Handle: | http://hdl.handle.net/11562/736004 |
| Appare nelle tipologie: | 01.01 Articolo in Rivista |
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