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%).

A practical synthetic route to functionalized THBCs and oxygenated analogues via intramolecular Friedel-Crafts reactions

PICCINELLI, FABIO;
2006-01-01

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%).
2006
TETRAHYDRO-BETA-CARBOLINES; OLEFIN CROSS-METATHESIS; STEREOSELECTIVE ALKYLATION
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11562/736004
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