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Catalytic enantioselective addition of indoles to arylnitroalkenes: An effective route to enantiomerically enriched tryptamine precursors
Author(s) -
Bandini Marco,
Garelli Andrea,
Rovinetti Matteo,
Tommasi Simona,
UmaniRonchi Achille
Publication year - 2005
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20189
Subject(s) - chemistry , enantioselective synthesis , tryptamine , catalysis , combinatorial chemistry , organic chemistry , stereochemistry , biochemistry
A new valuable catalytic protocol for the preparation of synthetically useful β‐indolyl nitro compounds bearing benzhydryl stereocenters is presented. The combined use of catalytic amounts of a commercially available chiral [SalenAlCl] complex and pyridine allowed, for the Friedel–Crafts alkylation reaction of indoles with aromatic nitro‐olefins to be carried out in good yields and enantioselectivity (up to 63% ee). © 2005 Wiley‐Liss, Inc. Chirality 17:522–529, 2005.