Enantioselective Tsuji‐Trost α‐Fluoroallylation of Amino Acid Esters with Gem‐Difluorinated Cyclopropanes DOI
Zhengquan Su,

Binhong Tan,

Hui He

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(23)

Published: Feb. 27, 2024

Abstract A novel enantioselective Tsuji–Trost‐type cross coupling reaction between gem ‐difluorinated cyclopropanes and N ‐unprotected amino acid esters enabled by synergistic Pd/Ni/chiral aldehyde catalysis is presented herein. This transformation streamlined the diversity‐oriented synthesis (DOS) of optically active α‐quaternary α‐amino bearing a linear 2‐fluoroallylic motif, which served as an appealing platform for construction other valuable enantioenriched compounds. The key intermediates were confirmed HRMS detection, while DFT calculations revealed that excellent enantioselectivity was attributed to stabilizing non‐covalent interactions Pd(II)‐π‐fluoroallyl species Ni(II)‐Schiff base complex.

Language: Английский

Enantioselective Tsuji‐Trost α‐Fluoroallylation of Amino Acid Esters with Gem‐Difluorinated Cyclopropanes DOI
Zheng Su,

Binhong Tan,

Hui He

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(23)

Published: Feb. 27, 2024

A novel enantioselective Tsuji-Trost-type cross coupling reaction between gem-difluorinated cyclopropanes and N-unprotected amino acid esters enabled by synergistic Pd/Ni/chiral aldehyde catalysis is presented herein. This transformation streamlined the diversity-oriented synthesis (DOS) of optically active α-quaternary α-amino bearing a linear 2-fluoroallylic motif, which served as an appealing platform for construction other valuable enantioenriched compounds. The key intermediates were confirmed HRMS detection, while DFT calculations revealed that excellent enantioselectivity was attributed to stabilizing non-covalent interactions Pd(II)-π-fluoroallyl species Ni(II)-Schiff base complex.

Language: Английский

Citations

11
Palladium/Amine Dual-Catalyzed Tsuji–Trost Fluoroallylation of Aldehydes with gem-Difluorinated Cyclopropanes DOI
Zhengquan Su,

Binhong Tan,

Zhaodong Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(25), P. 5375 - 5379

Published: June 12, 2024

We herein disclose the Pd/amine dual-catalyzed ring-opening cross-coupling reaction between

Language: Английский

Citations

5
Synergistic Pd/Ni Dual-Catalyzed Cross-Coupling of Azaaryl Acetates with gem-Difluorinated Cyclopropanes DOI
Xuexue Zhang,

H. HELEN LIN,

Binhong Tan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(41), P. 8956 - 8960

Published: Oct. 7, 2024

We herein report the development of a novel Pd/Ni dual-catalyzed ring-opening functionalization

Language: Английский

Citations

5
Ruthenium-catalyzed C–H functionalization of indoles and indolines with 7-azabenzonorbornadienes: access to aminodihydronaphthyl indoles and indolines DOI

Jia-Zhen Chen,

Zhong‐Xia Wang

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(25), P. 5159 - 5169

Published: Jan. 1, 2024

An Ru-catalyzed carbamoyl-directed C–H functionalization of indoles and indolines with 7-azabenzonorbornadienes results in 2-aminodihydronaphthyl 7-aminodihydronaphthyl indolines, respectively.

Language: Английский

Citations

4
Electrocatalytic Enantioselective Tandem C–H Indolization toward Biindolyl Atropisomers: Reaction Development and Mechanistic Insight DOI

Zhi‐Huan Peng,

Ping Huang, Ao-Long Li

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: 15(3), P. 1422 - 1430

Published: Jan. 9, 2025

The electrochemical methods for asymmetric indolization are still elusive and pose a significant challenge. Taking advantage of 2-alkynylanilines as electrochemically compatible indolyl equivalents, we herein represent mild highly enantioselective electrocatalytic process tandem C–H to form 2,3′-biindolyl atropisomers along with hydrogen evolution reaction. Integrated experimental computational mechanistic studies revealed that sequential metalation/nucleophilic cyclization/reductive elimination/anodic oxidation sequence involving RhIII–RhI–RhIII catalytic cycle accounts the established transformation.

Language: Английский

Citations

0
Palladium-Catalyzed Dearomative Fluoroallylation of Pyrroles with gem-Difluorinated Cyclopropanes DOI
Long Gu, Fajie Duan,

Jiafeng Ye

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 26, 2025

We herein report the development of a novel Pd-catalyzed dearomative functionalization pyrroles with gem-difluorinated cyclopropanes (gem-F2CPs). This dearomative/ring-opening strategy streamlines diversity-oriented synthesis (DOS) α-quaternary 2-fluoroallylic 2H-pyrroles broad scope and excellent functional group tolerance, which enables efficient late-stage transformation complex bioactive molecule-derived gem-F2CPs. Derivation resulting fluoroallylic to different synthetically useful 2H-pyrrole motifs demonstrated synthetic value this methodology.

Language: Английский

Citations

0
Mo-Mediated Reductive Cyclization/Allylation of 2-Alkynyl Nitroarenes with 1,3-Dienes: Synthesis of 3-Allylindoles DOI

Jia-Yi Feng,

Jian-Bang Hu,

Yi Liu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 28, 2025

3-Allylindoles constitute a key structural feature in many natural products and bioactive compounds. In this work, we developed Mo-mediated reductive cyclization/allylation of 2-alkynyl nitroarenes with 1,3-dienes. Using Mo(CO)6 as both the reductant catalyst, broad range functionalized 3-allylindoles were prepared good to excellent yields from easily available 2-alkynylnitroarenes 1,3-dienes starting materials.

Language: Английский

Citations

0
Palladium(II)-Catalyzed Enantioselective Ring Opening of Oxabenzonorbornadienes via Domino Aminopalladation of Alkynylanilines DOI
Qianru Liu,

Junjie Meng,

Binhong Tan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 27(1), P. 369 - 375

Published: Dec. 30, 2024

We report herein a robust enantioselective ring opening coupling of oxabenzonorbornadienes via Pd(II)-catalyzed domino cyclization alkynylanilines, which features the formation three covalent bonds and two contiguous stereocenters with excellent enantio- diastereoselectivity broad substrate scope. The good functional group tolerance this desymmetrization strategy enables efficient late-stage transformation natural product-derived alkynylanilines. resulting indolated dihydronaphthols could serve as valuable platform to streamline diversity-oriented synthesis other enantioenriched tetrahydronaphthalene derivatives.

Language: Английский

Citations

1
Enantioselective Tsuji‐Trost α‐Fluoroallylation of Amino Acid Esters with Gem‐Difluorinated Cyclopropanes DOI
Zhengquan Su,

Binhong Tan,

Hui He

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(23)

Published: Feb. 27, 2024

Abstract A novel enantioselective Tsuji–Trost‐type cross coupling reaction between gem ‐difluorinated cyclopropanes and N ‐unprotected amino acid esters enabled by synergistic Pd/Ni/chiral aldehyde catalysis is presented herein. This transformation streamlined the diversity‐oriented synthesis (DOS) of optically active α‐quaternary α‐amino bearing a linear 2‐fluoroallylic motif, which served as an appealing platform for construction other valuable enantioenriched compounds. The key intermediates were confirmed HRMS detection, while DFT calculations revealed that excellent enantioselectivity was attributed to stabilizing non‐covalent interactions Pd(II)‐π‐fluoroallyl species Ni(II)‐Schiff base complex.

Language: Английский

Citations

0