Organocatalytic Asymmetric Annulation of ortho-Alkynylanilines: Synthesis of Axially Chiral Naphthyl-C2-Indoles.

08:00 EDT 11th September 2019 | BioPortfolio

Summary of "Organocatalytic Asymmetric Annulation of ortho-Alkynylanilines: Synthesis of Axially Chiral Naphthyl-C2-Indoles."

A chiral Brønsted base-catalyzed asymmetric annulation of ortho-alkynylanilines has been developed to access axially chiral naphthyl-C2-indoles through vinylidene ortho-quinone methides (VQMs) intermediates. This strategy provides a unique organocatalytic atroposelective route to axially chiral aryl-C2-indole skeletons with excellent enantioselectivity and functional group tolerance. This transformation was applicable to the deca-gram preparation (50.0 g) with perfect enantioselectivity through simple recrystallization. Moreover, the utility of this reaction had been demonstrated by a variety of transformations towards the prepared chiral naphthyl-C2-indoles for a series of carbon-heteroatom bonds formation. Furthermore, the prepared axially chiral naphthyl-C2-indoles had been applied as chiral skeleton for organocatalytic aza-Baylis-Hillman reaction and asymmetric formal [4+2] tandem cyclization to give corresponding adducts in high yields with improved enantioselectivities and diastereoselectivities.


Journal Details

This article was published in the following journal.

Name: Angewandte Chemie (International ed. in English)
ISSN: 1521-3773


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