Topics

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.

Affiliation

Journal Details

This article was published in the following journal.

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

Links

DeepDyve research library

PubMed Articles [5840 Associated PubMed Articles listed on BioPortfolio]

Recent advances in the synthesis of axially chiral biaryls via transition metal-catalysed asymmetric C-H functionalization.

Axially chiral biaryl motifs are widely present in natural products and pharmaceuticals. Moreover, they have been broadly used as privileged ligands in asymmetric catalysis. Over the past few decades,...

Enantioselective Synthesis of C-N Axially Chiral N-Aryloxindoles by Asymmetric Rhodium-Catalyzed Dual C-H Activation.

The first enantioselective Satoh-Miura type reaction is reported. A variety of C-N axially chiral N-aryloxindoles have been enantioselectively synthesized by an asymmetric rhodium-catalyzed dual C-H a...

Asymmetric Synthesis of Chiral 1,4-Enynes via Organocatalytic Alkenylation of Propargyl Alcohols with Trialkenylboroxines.

A highly enantioselective synthesis of 1,4-enynes is described via an organocatalytic reaction between propargyl alcohols and trialkenylboroxines. Our strategy relies on the acid-mediated generation o...

Organocatalytic Enantio- and Diastereoselective Construction of syn-1,3-Diol Motifs via Dynamic Kinetic Resolution of In Situ Generated Chiral Cyanohydrins.

An organocatalytic method for the asymmetric synthesis of syn-1,3-dioxanes as protected 1,3-diols via dynamic kinetic resolution of in situ generated chiral cyanohydrins has been developed. This metho...

Pd(II)-Catalyzed Asymmetric Oxidative Annulation of N-Alkoxyheteroaryl Amides and 1,3-Dienes.

The first Pd(II)-catalyzed asymmetric oxidative annulation of N-alkoxyaryl amides and 1,3-dienes is reported, which features particular applicability for quick assembly of different types of chiral he...

Clinical Trials [529 Associated Clinical Trials listed on BioPortfolio]

Orthokeratology for High Myopia (OHM) Study

This project aims to investigate/examine high myopic subjects on full correction ortho-k (using Topaz ortho-k lenses for high myopia) compared to subjects undergoing partial reduction orth...

To Compare SH T00658ID Over Ortho Tri-Cyclen Lo (US/Canada)

The objective of the study is to compare the oral contraceptive (OC) SH T00658ID over Ortho Tri-Cyclen Lo administered for 13 cycles to healthy female volunteers between 18 and 50 years of...

Combined Atropine With Orthokeratology in Childhood Myopia Control (AOK) -A Randomized Controlled Trial

This study aims to compare effects in retardation of myopia progression of combined ortho-k and 0.01% atropine therapy with those of ortho-k alone.Myopia control methods mainly focus on op...

Investigation of the Effect of Short-term Orthokeratology With Increased Compression Factor on Ocular Parameters

Orthokeratology (ortho-k) is a clinical technique that uses reverse geometry rigid gas permeable contact lens exerting positive pressure on the central cornea to temporary reduce refractiv...

Study to Assess the Effect of BMS-790052 on the Pharmacokinetics of Ortho Tri-Cyclen® in Healthy Female Subjects

The purpose of this study is to assess the effect of BMS-790052 on the pharmacokinetics of Ortho Tri-Cyclen® in healthy female subjects.

Medical and Biotech [MESH] Definitions

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.

Quick Search


DeepDyve research library

Searches Linking to this Article