Iodine Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights DOI Creative Commons

Domenic Pace,

Raphaël Robidas, Uyen P. N. Tran

et al.

Published: July 6, 2020

Substituted pyrans and furans are core structures found in a wide variety of natural products biologically-active compounds. Herein, we report practical mild catalytic method for the synthesis substituted using molecular iodine, simple inexpensive catalyst. The described herein is performed solvent-free conditions ambient temperature atmosphere, thus offering facile green alternative to currently available reaction protocols. A combination experimental studies high‐level DFT calculations revealed interesting mechanistic insights this seemingly reaction.

Language: Английский

Rhodium‐Catalyzed Asymmetric Hydrogenation of 3‐Benzoylaminocoumarins for the Synthesis of Chiral 3‐Amino Dihydrocoumarins DOI
Yunnan Xu, Delong Liu, Yu Deng

et al.

Angewandte Chemie, Journal Year: 2021, Volume and Issue: 133(44), P. 23794 - 23799

Published: Oct. 1, 2021

Abstract An asymmetric hydrogenation of 3‐benzoylaminocoumarins was achieved for the first time using our BridgePhos‐Rh catalytic system, providing chiral 3‐amino dihydrocoumarins in high yields (up to 98 %) and with excellent enantioselectivities 99.7 % ee ). The relationship between hydrogenations dihedral angles resulting π‐π stacking effects complexes, which were determined by X‐ray diffraction analysis, are discussed. corresponding hydrogenated products allow many transformations, several skeletons important physiological pharmacological activities.

Language: Английский

Citations

4
Diastereo‐ and Enantioselective Synthesis of Bisbenzannulated Spiroketals and Spiroaminals by Ir/Ag/Acid Ternary Catalysis DOI
Wu‐Lin Yang,

Xin‐Yu Shang,

Tao Ni

et al.

Angewandte Chemie, Journal Year: 2022, Volume and Issue: 134(42)

Published: Aug. 4, 2022

Abstract We reported herein an iridium/silver/acid ternary catalytic system to access bisbenzannulated [6,6]‐spiroketals in high efficiency with generally diastereo‐ and enantioselectivities (up >20 : 1 dr, >99 % ee). In this procedure, readily available o ‐alkynylacetophenones undergo cycloisomerization generate isochromenes situ that participate stereoselective allylation/spiroketalization sequence 2‐(1‐hydroxyallyl)phenols. Meanwhile, 2‐(1‐hydroxyallyl)anilines were also compatible cascade reaction, furnishing structurally novel [6,6]‐spiroaminals good diastereoselectivities (8 1–12 dr) excellent (98 %–>99 Moreover, experimental studies theoretical calculations performed illustrate the reaction mechanism stereochemistry.

Language: Английский

Citations

2
Further Studies on the Gold-Catalyzed Oxidative Domino Cyclization/Cycloaddition to Give Polyfunctional Tetracycles DOI Open Access
Peter Metz,

Tobias Groß,

Korany A. Ali

et al.

Heterocycles, Journal Year: 2018, Volume and Issue: 99(2), P. 1170 - 1170

Published: Dec. 26, 2018

6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0 Chemical Shift (ppm) 6.89 2.97 2.00 2.

Language: Английский

Citations

0
Iodine Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights DOI Creative Commons

Domenic Pace,

Raphaël Robidas, Uyen P. N. Tran

et al.

Published: July 6, 2020

Substituted pyrans and furans are core structures found in a wide variety of natural products biologically-active compounds. Herein, we report practical mild catalytic method for the synthesis substituted using molecular iodine, simple inexpensive catalyst. The described herein is performed solvent-free conditions ambient temperature atmosphere, thus offering facile green alternative to currently available reaction protocols. A combination experimental studies high‐level DFT calculations revealed interesting mechanistic insights this seemingly reaction.

Language: Английский

Citations

0
Iodine Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights DOI Creative Commons

Domenic Pace,

Raphaël Robidas, Uyen P. N. Tran

et al.

Published: July 6, 2020

Substituted pyrans and furans are core structures found in a wide variety of natural products biologically-active compounds. Herein, we report practical mild catalytic method for the synthesis substituted using molecular iodine, simple inexpensive catalyst. The described herein is performed solvent-free conditions ambient temperature atmosphere, thus offering facile green alternative to currently available reaction protocols. A combination experimental studies high‐level DFT calculations revealed interesting mechanistic insights this seemingly reaction.

Language: Английский

Citations

0