Gold-catalyzed enantioselective functionalization of indoles DOI

Pierre Milcendeau,

Nazarii Sabat, Angélique Ferry

et al.

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(31), P. 6006 - 6017

Published: Jan. 1, 2020

This review documents the potential of enantioselective gold catalysis for functionalization indoles.

Language: Английский

Asymmetric gold catalysis enabled by specially designed ligands DOI
Amol B. Gade,

Urvashi Urvashi,

Nitin T. Patil

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1858 - 1895

Published: Jan. 1, 2024

This review is planned to provide a comprehensive overview of the progress made in design and development chiral ligands for asymmetric gold catalysis.

Language: Английский

Citations

13
Enantioselective and Regioselective Hydroetherification of Alkynes by Gold-Catalyzed Desymmetrization of Prochiral Phenols with P-Stereogenic Centers DOI
Yin Zheng, Linna Guo, Weiwei Zi

et al.

Organic Letters, Journal Year: 2018, Volume and Issue: 20(22), P. 7039 - 7043

Published: Oct. 29, 2018

The gold(I)-catalyzed enantioselective hydroetherification of alkynes was achieved via desymmetrization prochiral bisphenols bearing P-stereogenic centers. (S)-DTBM-Segphos(AuCl)2/AgNTf2 proved to be a highly efficient catalyst system for this transformation, affording P-chiral cyclic phosphine oxides in good yields with high enantioselectivities (with up 99% ee). same allowed the dialkynes. Synthetic transformations cyclization products afforded other molecules enantiospecificity.

Language: Английский

Citations

75
Enantioselective Folding of Enynes by Gold(I) Catalysts with a Remote C2-Chiral Element DOI
Giuseppe Zuccarello,

Joan G. Mayans,

Imma Escofet

et al.

Journal of the American Chemical Society, Journal Year: 2019, Volume and Issue: 141(30), P. 11858 - 11863

Published: July 10, 2019

Chiral gold(I) catalysts have been designed based on a modified JohnPhos ligand with distal C2-2,5-diarylpyrrolidine that creates tight binding cavity. The C2-chiral element is close to where the C–C bond formation takes place in cyclizations of 1,6-enynes. These chiral mononuclear applied for enantioselective 5-exo-dig and 6-endo-dig cyclization different 1,6-enynes as well first total synthesis three members carexane family natural products. Opposite enantioselectivities achieved seemingly analogous reactions 1,6-enynes, which result from folding substrates attractive aryl–aryl interactions.

Language: Английский

Citations

75
Enantioselective Synthesis of Isoxazolines Enabled by Palladium‐Catalyzed Carboetherification of Alkenyl Oximes DOI
Lei Wang, Kenan Zhang, Yuzhuo Wang

et al.

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 59(11), P. 4421 - 4427

Published: Dec. 23, 2019

Reported here is a highly efficient Pd/Xiang-Phos catalyzed enantioselective carboetherification of alkenyl oximes with either aryl or halides, delivering various chiral 3,5-disubstituted and 3,5,5-trisubstituted isoxazolines in good yields up to 97 % ee. The sterically bulky electron-rich (S,Rs)-NMe-X2 ligand responsible for the excellent reactivities enantioselectivities. salient features this transformation include mild reaction conditions, general substrate scope, functional-group tolerance, yields, high enantioselectivities, easy scale-up, application late-stage modification bioactive compounds. obtained products can be readily transformed into useful 1,3-aminoalcohols.

Language: Английский

Citations

75
Gold-catalyzed enantioselective functionalization of indoles DOI

Pierre Milcendeau,

Nazarii Sabat, Angélique Ferry

et al.

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(31), P. 6006 - 6017

Published: Jan. 1, 2020

This review documents the potential of enantioselective gold catalysis for functionalization indoles.

Language: Английский

Citations

58