N-Heterocyclic carbene-catalyzed cascade reaction of 2-aroylvinylcinnamaldehydes with 2-aroylvinylchalcones: rapid assembly of six contiguous stereogenic centers with high diastereoselectivity

N-Heterocyclic carbene-catalyzed reaction of 2-aroylvinylcinnamaldehydes with 2-aroylvinylchalcones proceeded via a triple Michael addition and intramolecular lactonization cascade to produce novel 9-(2-aroyl-3-aroylmethyl-1-indanyl)-3-arylindeno[2,1- c ]pyran-1-ones in good yields with high diaster...

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Published in:Organic & biomolecular chemistry 2014-01, Vol.12 (1), p.123-131
Main Authors: Fan, Xing-Wen, Cheng, Ying
Format: Article
Language:English
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Summary:N-Heterocyclic carbene-catalyzed reaction of 2-aroylvinylcinnamaldehydes with 2-aroylvinylchalcones proceeded via a triple Michael addition and intramolecular lactonization cascade to produce novel 9-(2-aroyl-3-aroylmethyl-1-indanyl)-3-arylindeno[2,1- c ]pyran-1-ones in good yields with high diastereoselectivity. This reaction constructed six contiguous stereogenic centers in a single reactive event. Among 32 possible diastereoisomers that contain six stereocenters, only two diastereoisomers were detected with diastereomeric ratios being 10 : 1-28 : 1. This work opens up a new avenue for the synthesis of complex indane derivatives, a type of compound that has been reported to possess various biological and pharmaceutical activities. NHC-catalyzed reaction of 2-aroylvinylcinnamaldehydes with 2-aroylvinylchalcones produced good yields of novel 9-(2-aroyl-3-aroylmethyl-1-indanyl)-3-arylindeno[2,1- c ]pyran-1-ones with high diastereoselectivity.
ISSN:1477-0520
1477-0539
DOI:10.1039/c3ob41656a