Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 3, Issue 14, Pages 2566-2571Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b505220c
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The enantioselective Friedel-Crafts addition of indoles to nitro-olefins using chiral hydrogen-bonding bis-sulfonamides as the catalysts has been developed. The reactions, in the presence of only 2 mol% catalyst, generally proceed in high yields and with enantioselectivities up to 64% ee, and the enantiomeric excess can be improved to > 98% ee by recrystallization. Various synthetic transformations of the Friedel-Crafts adducts are demonstrated: the nitro group can easily be reduced to the corresponding amine and the product obtained can undergo a stereocontrolled Pictet-Spengler cyclization to give, for example, enantiopure tetrahydro-beta-carbolines. The X-ray structure of the chiral bis-sulfonamides has been determined and based on these structures the mechanism for the stereoselectivity in the reaction is discussed.
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