N-heterocyclic carbene-catalyzed enantioselective annulation of indolin-3-ones with bromoenals

Chem Asian J. 2014 Jun;9(6):1535-8. doi: 10.1002/asia.201402052. Epub 2014 Apr 11.

Abstract

N-Heterocyclic carbene-catalyzed reactions of indolin-3-ones with 2-bromoenals opened an asymmetric access to 3,4-dihydropyrano[3,2-b]indol-2(5 H)-ones in good yields and with good to excellent enantioselectivities. This protocol tolerates a broad substrate scope. In addition, a possible mechanism for the annulation reaction is presented.

Keywords: N-heterocyclic carbenes; annulation; asymmetric synthesis; dihydropyranoindol-2-ones; organocatalysis.