Synthesis of Forms of a Chiral Ruthenium Complex Containing a Ru–Colefin(sp2) Bond and Their Application to Catalytic Asymmetric Cyclopropanation Reactions DOI
Hayato Inoue, Nga Phan Thi Thanh, Ikuhide Fujisawa

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(4), P. 1475 - 1479

Published: Jan. 28, 2020

Organometallic complexes [Ru-Colefin(sp2)-Ru(II)-Pheox 2a-2d] containing a Ru-Colefin(sp2) bond have been prepared from unsaturated chiral oxazoline derivatives and evaluated for asymmetric cyclopropanation reactions. The corresponding optically active cyclopropanes were obtained with high yields stereoselectivities (≥99/<1 trans/cis, 99% trans ee). enantioselectivities found to be affected by the geminal substituent on Ru-C(sp2) bond. In particular, Ru(II)-Prox catalyst 2c, in which there was no metal, shown highest enantioselectivities.

Language: Английский

Gold-Catalyzed Synthesis of Small Rings DOI Creative Commons
Mauro Mato, Allegra Franchino, Cristina García‐Morales

et al.

Chemical Reviews, Journal Year: 2020, Volume and Issue: 121(14), P. 8613 - 8684

Published: Nov. 2, 2020

Three- and four-membered rings, widespread motifs in nature medicinal chemistry, have fascinated chemists ever since their discovery. However, due to energetic considerations, small rings are often difficult assemble. In this regard, homogeneous gold catalysis has emerged as a powerful tool construct these highly strained carbocycles. This review aims provide comprehensive summary of all the major advances discoveries made gold-catalyzed synthesis cyclopropanes, cyclopropenes, cyclobutanes, cyclobutenes, corresponding heterocyclic or heterosubstituted analogs.

Language: Английский

Citations

185

Catalytic enantioselective construction of vicinal quaternary carbon stereocenters DOI Creative Commons
Feng Zhou, Lei Zhu, Bo‐Wen Pan

et al.

Chemical Science, Journal Year: 2020, Volume and Issue: 11(35), P. 9341 - 9365

Published: Jan. 1, 2020

This review summarizes the advances in catalytic enantioselective construction of vicinal quaternary carbon stereocenters, introduces major synthetic strategies and discusses their advantages limitations, outlines opportunities.

Language: Английский

Citations

129

Pd/PC‐Phos‐Catalyzed Enantioselective Intermolecular Denitrogenative Cyclization of Benzotriazoles with Allenes and N‐Allenamides DOI
Peichao Zhang, Jie Han, Junliang Zhang

et al.

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(33), P. 11444 - 11448

Published: June 14, 2019

Abstract Reported herein is an asymmetric Pd/PC‐Phos‐catalyzed denitrogenative cyclization of benzotriazoles with allenes and N‐allenamides, representing the first example enantioselective cyclizations benzotriazoles. A series optically active 3‐methyleneindolines were obtained in good yields high ee values. The use inexpensive readily available starting materials, regio‐ enantioselectivity, a broad substrate scope, mild reaction conditions, no need for base, as well versatile functionalization make this approach attractive.

Language: Английский

Citations

90

Design and Synthesis of TY‐Phos and Application in Palladium‐Catalyzed Enantioselective Fluoroarylation ofgem‐Difluoroalkenes DOI
Tao‐Yan Lin,

Zhangjin Pan,

Youshao Tu

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(51), P. 22957 - 22962

Published: Sept. 25, 2020

Abstract The first example of highly enantioselective fluoroarylation gem‐difluoroalkenes with aryl halides is presented by using a new chiral sulfinamide phosphine ( Sadphos ) type ligand TY‐Phos . N‐Me‐ can be easily synthesized on gram scale from readily available starting materials in three steps. Salient features this work including materials, good yields, high enantioselectivities as well broad substrate scope make approach very practical and attractive. Notably, the asymmetric synthesis an analogue biologically active molecule also reported.

Language: Английский

Citations

80

Recent Advances in the Development of Chiral Gold Complexes for Catalytic Asymmetric Catalysis DOI
Jia‐Jun Jiang, Man‐Kin Wong

Chemistry - An Asian Journal, Journal Year: 2021, Volume and Issue: 16(5), P. 364 - 377

Published: Jan. 2, 2021

Asymmetric gold catalysis has been rapidly developed in the past ten years. Breakthroughs have made by rational design and meticulous selection of chiral ligands. This review summarizes newly gold-catalyzed enantioselective organic transformations recent progress ligand (since 2016), organized according to different types ligands, including bisphosphine monophosphine phosphite-derived N-heterocyclic carbene ligands for asymmetric gold(I) as well heterocyclic oxazoline gold(III) catalysis.

Language: Английский

Citations

73

Asymmetric Dearomatization of Indole by Palladium/PC‐Phos‐Catalyzed Dynamic Kinetic Transformation DOI
Haoke Chu, Jie Cheng, Junfeng Yang

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(49), P. 21991 - 21996

Published: Sept. 2, 2020

Abstract A palladium‐catalyzed intermolecular dynamic kinetic asymmetric dearomatization of 3‐arylindoles with internal alkynes was developed the use achiral Xantphos and chiral sulfinamide phosphine ligand ( PC‐Phos ) as co‐ligands. This method could deliver various spiro[indene‐1,3′‐indole] compounds in good yields (up to 95 % yield) up 98 ee . The salient features transformation include readily available substrates, ease scale‐up versatile functionalization products. mechanistic experiments gave some insights on active intermediates.

Language: Английский

Citations

71

Palladium/TY-Phos-Catalyzed Asymmetric Heck/Tsuji–Trost Reaction of o-Bromophenols with 1,3-Dienes DOI

Youshao Tu,

Bing Xu, Qian Wang

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(8), P. 4378 - 4383

Published: Feb. 16, 2023

2,3-Dihydrobenzofurans are crucial building blocks in the synthesis of natural products and pharmaceutical molecules. However, their asymmetric has been a long-standing formidable challenge so far. In this work, we developed highly enantioselective Pd/TY-Phos-catalyzed Heck/Tsuji-Trost reaction o-bromophenols with various 1,3-dienes, allowing expedient access to chiral substituted 2,3-dihydrobenzofurans. This features excellent regio- enantiocontrol, high functional group tolerance, easy scalability. More importantly, demonstration method as valuable tool for construction optically pure (R)-tremetone fomannoxin is highlighted.

Language: Английский

Citations

28

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 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