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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.
This article was published in the following journal.
Name: Angewandte Chemie (International ed. in English)
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Polymers of N-SUBSTITUTED GLYCINES containing chiral centers at the a-position of their side chains. These oligomers lack HYDROGEN BONDING donors, preventing formation of the usual intrachain hydrogen bonds but can form helices driven by the steric influence of chiral side chains.
One ring heterocyclic compounds defined by C6H7NO. Permitted are any degree of hydrogenation, any substituents and any ortho-fused or ortho-peri-fused ring systems.
Enzymes that catalyze the epimerization of chiral centers within carbohydrates or their derivatives. EC 5.1.3.
Enzymes that catalyze either the racemization or epimerization of chiral centers within amino acids or derivatives. EC 5.1.1.
A general class of ortho-dihydroxyphenylalkylamines derived from tyrosine.