Enantioselective Synthesis of Fused Polycyclic Tropanes via Dearomative [3 + 2] Cycloaddition Reactions of 2-Nitrobenzofurans DOI
Zhen Wang, Dong‐Chao Wang, Ming‐Sheng Xie

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 22(1), P. 164 - 167

Published: Dec. 23, 2019

A straight synthetic approach to fused polycyclic tropane scaffold formation through an asymmetric dearomatization cycloaddition process of 2-nitrobenzofurans with cyclic azomethine ylides was successfully developed. In the presence a chiral copper complex, derived from Cu(OAc)2 and diphosphine ligand, series derivatives were obtained in high yields (75–91%) excellent enantioselectivities (90–98%). The utility this method showcased by facile transformation product.

Language: Английский

A novel type of donor–acceptor cyclopropane with fluorine as the donor: (3 + 2)-cycloadditions with carbonyls DOI Creative Commons
Haidong Liu, Lifang Tian, Hui Wang

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 13(9), P. 2686 - 2691

Published: Jan. 1, 2022

A new type of donor–acceptor cyclopropane with gem -difluorine as an unconventional donor group undergoes (3 + 2)-cycloadditions various aldehydes/ketones, affording densely functionalized -difluorotetrahydrofurans.

Language: Английский

Citations

33

Chiral Aldehyde–Palladium Catalysis Enables Asymmetric Synthesis of α-Alkyl Tryptophans via Cascade Heck-Alkylation Reaction DOI

Qi-Wen Shen,

Wen Wei,

Qi‐Xiang Guo

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(17), P. 3163 - 3167

Published: April 25, 2023

The first catalytic asymmetric cascade Heck-alkylation reaction of NH2-unprotected amino acid esters with N-(2-iodophenyl)allenamides is reported in this work. Under the promotion a combining system comprising chiral aldehyde, palladium complex, and Lewis ZnCl2, title takes place smoothly, giving optically active α-alkyl tryptophan derivatives moderate to good yields excellent enantioselectivities. target products can be converted into other structurally complex indoles without loss

Language: Английский

Citations

17

Enantioselective Synthesis of Oxazocines via MQ‐Phos Enabled Palladium‐Catalyzed Asymmetric Formal [4+4]‐Cycloadditions DOI Creative Commons

Qingcheng Meng,

Yinggao Meng,

Qinglin Liu

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: 11(31)

Published: June 17, 2024

Abstract Oxazocines are key structural intermediates in the synthesis of natural products and pharmaceutical molecules. However, oxazocines especially a highly enantioselective manner, is long‐standing formidable challenge due to unfavorable energetics involved cyclization. Herein, series new PNP‐Ligand P ‐chiral stereocenter first designed synthesized, called MQ‐Phos , successfully applied it Pd‐catalyzed higher‐order formal [4+4]‐cycloaddition α β ‐unsaturated imines with 2‐(hydroxymethyl)‐1‐arylallyl carbonates. The reaction features mild conditions, excellent regio‐ enantiocontrol broad substrate scope (54 examples). Various medium‐sized rings can be afforded moderate yields (up 92%) enantioselectivity 99% ee). newly developed critical for ring catalytic reactivity enantioselectivity.

Language: Английский

Citations

6

Enantioselective dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita–Baylis–Hillman carbonates DOI

Xin-He Yang,

Jianping Li, Dong‐Chao Wang

et al.

Chemical Communications, Journal Year: 2019, Volume and Issue: 55(62), P. 9144 - 9147

Published: Jan. 1, 2019

The phosphine-catalyzed asymmetric dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman (MBH) carbonates or allenoate was developed. reaction MBH resulted in a series cyclopentabenzofurans containing three contiguous stereocenters good to high yields, diastereoselectivities and enantioselectivities. use also gave the target product moderate enantioselectivity.

Language: Английский

Citations

52

Enantioselective Synthesis of Fused Polycyclic Tropanes via Dearomative [3 + 2] Cycloaddition Reactions of 2-Nitrobenzofurans DOI
Zhen Wang, Dong‐Chao Wang, Ming‐Sheng Xie

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 22(1), P. 164 - 167

Published: Dec. 23, 2019

A straight synthetic approach to fused polycyclic tropane scaffold formation through an asymmetric dearomatization cycloaddition process of 2-nitrobenzofurans with cyclic azomethine ylides was successfully developed. In the presence a chiral copper complex, derived from Cu(OAc)2 and diphosphine ligand, series derivatives were obtained in high yields (75–91%) excellent enantioselectivities (90–98%). The utility this method showcased by facile transformation product.

Language: Английский

Citations

52