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2005
Indole derivatives
R 0140
Enantioselective Friedel—Crafts Alkylation Reactions Catalyzed by a Chiral
Nonracemic C2-Symmetric 2,2'-Bipyridyl Copper(II) Complex. — The title proce30- 099 dure
represents the first application of a 2,2'-bipyridyl ligand in catalytic enantioselective Friedel—Crafts reactions. The active copper(II) catalyst, generated in situ, affords
esters (IV) in good yields and mostly high enantiomeric excess (up to 90% e.e.). The
reactions of indole (V) and 3-methoxyphenol (VIII) with ketoester (VI) is also highly
effective. Product (IX) is a novel chroman derivative, whose absolute stereochemistry
cannot be assigned. — (LYLE, M. P. A.; DRAPER, N. D.; WILSON*, P. D.; Org.
Lett. 7 (2005) 5, 901-904; Dep. Chem., Simon Fraser Univ., Burnaby, B. C. V5A 1S6,
Can.; Eng.) — R. Steudel
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