Journal
SYNLETT
Volume -, Issue 9, Pages 1289-1301Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0029-1219929
Keywords
chiral Bronsted acids; enantioselectivity; Friedel-Crafts reactions; indoles; organocatalysis
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Funding
- National Natural Science Foundation of China [20732006, 20821002, 20972177]
- National Basic Research Program of China [2009CB825300]
- Chinese Academy of Sciences
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The asymmetric Friedel-Crafts reaction of indoles is a synthetic methodology that enables direct access to the enantiopure indole derivatives. In this review, work mainly carried out by You and his co-workers on the regio- and enantioselective synthesis of indole derivatives will be discussed. Chiral Bronsted acids or iridium complexes promote highly enantioselective Friedel-Crafts reactions of indoles and 4,7-dihydroindoles starting with various electrophilic reagents, such as imines, N-tosyl-substituted amines, beta,gamma-unsaturated a-keto esters, nitro-substituted olefins, aldehydes, and allyl carbonates. These methodologies can be used to readily prepare diverse enantioenriched indoles, such as indol-3-ylmethanamines, indol-2-ylmethanamines, unsymmetrical arylbis(indol-3-yl)methanes, 9-indol-3-ylfluorenes, tetrahydropyrano[3,4-b]indoles, tetrahydro-gamma-carbolines, and tetrahydro-beta-carbolines.
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