Reduction of the indole ring system: synthesis of 4,5,6,7-tetrahydroindoles

Authors
McComas, CC Van Vranken, DL
Citation
Cc. Mccomas et Dl. Van Vranken, Reduction of the indole ring system: synthesis of 4,5,6,7-tetrahydroindoles, TETRAHEDR L, 40(46), 1999, pp. 8039-8043
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
46
Year of publication
1999
Pages
8039 - 8043
Database
ISI
SICI code
0040-4039(19991112)40:46<8039:ROTIRS>2.0.ZU;2-T
Abstract
A general two-step procedure for the reduction of indoles to the correspond ing 4,5,6,7-tetrahydroindoles has been developed. A regioselective Birch re duction followed by catalytic hydrogenation is employed to accomplish this transformation. Yields for the sensitive pyrrole products are typically bet ween 40 and 50%. This method provides access to complex chiral pyrroles tha t cannot be readily prepared by other methods. (C) 1999 Elsevier Science Lt d. All rights reserved.