Triazole‐Based Anion‐Binding Catalysis for the Enantioselective Dearomatization of N‐Heteroarenes with Phosphorus Nucleophiles DOI

Theresa Fischer,

Qui‐Nhi Duong,

Olga Garcı́a Mancheño

et al.

Chemistry - A European Journal, Journal Year: 2017, Volume and Issue: 23(25), P. 5983 - 5987

Published: Jan. 23, 2017

Abstract The first enantioselective synthesis of chiral heterocyclic α‐amino phosphonates by nucleophilic dearomatization quinolines and pyridines using an anion‐binding organocatalysis approach is described. Chiral tetrakistriazoles were employed as efficient hydrogen‐bond donor catalysts forming a close ion‐pair with the in situ formed N ‐acyl salts 2,2,2‐trichlorethoxycarbonyl chloride (TrocCl). was subsequently treated various phosphorus nucleophiles, such silyl‐protected dialkyl‐ trialkylphosphites. Thus, corresponding products obtained complete or high regioselectivities up to 97:3 e.r. for 89:11 more challenging pyridine substrates. This method allows rapid access substituted cyclic phosphonates, which can be easily transformed into phosphonic acid derivatives.

Language: Английский

Chiral ligands designed in China DOI Creative Commons
Yuanyuan Liu, Wenbo Li, Junliang Zhang

et al.

National Science Review, Journal Year: 2017, Volume and Issue: 4(3), P. 326 - 358

Published: May 1, 2017

Abstract Asymmetric catalysis has become an indispensable and productive field within the Chinese organic chemistry society. The design of chiral ligands is one most prominent research areas in this field. Since late 1990s, chemists have developed numerous possessing novel skeletons concepts. Some these been widely adopted can be regarded as ‘privileged ligand’, which shown excellent performance many asymmetric catalytic reactions. In review, we provide overview designed by scientists with aim promoting development area China hope encouraging more across world to use when designing

Language: Английский

Citations

72

Enantioselective Iridium-Catalyzed Allylic Cyclizations DOI
Michael A. Schafroth, Stephan M. Rummelt, David Šarlah

et al.

Organic Letters, Journal Year: 2017, Volume and Issue: 19(12), P. 3235 - 3238

Published: June 2, 2017

A method for the enantioselective synthesis of carbo- and heterocyclic ring systems enabled through combination Lewis acid activation iridium-catalyzed allylic substitution is described. The reaction proceeds with branched, alcohols carbon nucleophiles as well heteronucleophiles to give a diverse set in good yields high enantioselectivities. utility highlighted by asymmetric syntheses erythrococcamides B.

Language: Английский

Citations

70

An Iridium(I) N‐Heterocyclic Carbene Complex Catalyzes Asymmetric Intramolecular Allylic Amination Reactions DOI
Ke‐Yin Ye, Qiang Cheng, Chun‐Xiang Zhuo

et al.

Angewandte Chemie International Edition, Journal Year: 2016, Volume and Issue: 55(28), P. 8113 - 8116

Published: May 10, 2016

A chiral iridium(I) N-heterocyclic carbene complex was reported for the first time as catalyst in highly enantioselective intramolecular allylic amination reaction. The current method provides facile access to biologically important enantioenriched indolopiperazinones and piperazinones good yields (74-91 %) excellent enantioselectivities (92-99 % ee). Preliminary mechanistic investigations reveal that C-H activation occurs at position ortho N-aryl group of ligand.

Language: Английский

Citations

69

Cu-catalyzed Asymmetric Dearomative [3 + 2] Cycloaddition Reaction of Benzazoles with Aminocyclopropanes DOI Creative Commons

Meng‐Cheng Zhang,

Dong‐Chao Wang, Ming‐Sheng Xie

et al.

Chem, Journal Year: 2018, Volume and Issue: 5(1), P. 156 - 167

Published: Oct. 25, 2018

Language: Английский

Citations

68

Triazole‐Based Anion‐Binding Catalysis for the Enantioselective Dearomatization of N‐Heteroarenes with Phosphorus Nucleophiles DOI

Theresa Fischer,

Qui‐Nhi Duong,

Olga Garcı́a Mancheño

et al.

Chemistry - A European Journal, Journal Year: 2017, Volume and Issue: 23(25), P. 5983 - 5987

Published: Jan. 23, 2017

Abstract The first enantioselective synthesis of chiral heterocyclic α‐amino phosphonates by nucleophilic dearomatization quinolines and pyridines using an anion‐binding organocatalysis approach is described. Chiral tetrakistriazoles were employed as efficient hydrogen‐bond donor catalysts forming a close ion‐pair with the in situ formed N ‐acyl salts 2,2,2‐trichlorethoxycarbonyl chloride (TrocCl). was subsequently treated various phosphorus nucleophiles, such silyl‐protected dialkyl‐ trialkylphosphites. Thus, corresponding products obtained complete or high regioselectivities up to 97:3 e.r. for 89:11 more challenging pyridine substrates. This method allows rapid access substituted cyclic phosphonates, which can be easily transformed into phosphonic acid derivatives.

Language: Английский

Citations

64