Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 349, Issue 11-12, Pages 1863-1867Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200700151
Keywords
asymmetric catalysis; Bronsted acid; enantioselectivity; Friedel-Crafts reaction; organic catalysis; phosphoric acid
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A highly enantioselective 1,2-aza-Friedel-Crafts reaction of N-tert-butyldimethylsilylindole with N-tert-butoxycarbonyl aromatic imines is demonstrated using a BINOL-derived monophosphoric acid catalyst. The present approach provides efficient access to 3-indolylmethaneamines with aryl substituents in excellent enantioselectivities (up to 98 % ee). An inversion in the sense of enantioselection was found between monophosphoric acid catalysts bearing different substituents introduced at the 3,3'-position of binaphthyl backbone. We also calculated the three-dimensional structure of the monophosphoric acid catalysts to speculate on the inversion of the stereochemical outcome.
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