ChemPlusChem, Journal Year: 2023, Volume and Issue: 88(10)
Published: Aug. 7, 2023
By combining tandem asymmetric gold catalysis and subsequent stereoconvergent hydrolysis of enol ester in a one-pot process, hydroxylated propargylic esters are converted into chiral β-oxygenated ketones with mostly good enantiomeric ratios largely to excellent yields. The product center is formed via stereoselective cyclization allenyl intermediate, which enabled by gold-ligand cooperation.
Language: Английский
Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(5), P. 1384 - 1396
Published: March 22, 2024
Language: Английский
Citations
10
Natural Product Reports, Journal Year: 2024, Volume and Issue: 41(7), P. 1091 - 1112
Published: Jan. 1, 2024
This review highlights a curated selection of publications utilizing homogeneous gold-catalyzed cycloaddition and cyclization reactions for the total synthesis natural products reported from 2016 to mid-2023.
Language: Английский
Citations
6
Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3252 - 3257
Published: April 8, 2024
A synthetic method to prepare dispiroheterocycles containing two all-carbon quaternary centers efficiently that relies on the gold(I)-catalyzed double spirocyclization of 3-ene-1,7-diyne esters is described. The suggested mechanism delineates a rare example dispirocyclization featuring 1,n-acyloxy shifts comprising 1,3-acyloxy migration and an interrupted 1,5-acyl was achieved with assistance residual water in reaction media.
Language: Английский
Citations
6
ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 5211 - 5218
Published: March 12, 2025
The asymmetric electrophilic amination using azodicarboxylates as the N-source for construction of C–N bond has attracted much attention over past decades. However, use in situ formed nucleophilic intermediates, rather than bench-stable reagents, remains elusive and challenging. Herein, we disclose an enantioselective reaction generated alkylgold species with under a gold complex chiral quinine-derived squaramide (QN-SQA) synergetic catalysis, leading to alkylideneoxazolines nitrogen-containing tertiary carbon stereocenter good high yields enantioselectivities. Moreover, starting from same oxazoles incorporating aminomethyl group on 5-position could be obtained by Brønsted acid relay catalysis via alkylideneoxazoline species. This method offers complementary approach through interception With this strategic protocol, further synthetic applications can envisioned catalytic C–C C–X bonds.
Language: Английский
Citations
0
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: March 18, 2025
An efficient synthetic method to regioselectively assemble masked 2-pyridones that relies on sequential gold-catalyzed cycloisomerization and phenyliodonium diacetate (PIDA)-mediated oxidative nitrogen insertion from 1,3-enynyl esters in a one-pot, two-step manner is described. The utility of the cascade protocol was further demonstrated by 2 mmol scale synthesis one example its elaboration other potentially useful building blocks as well late-stage modification diverse array structurally complex bioactive molecules.
Language: Английский
Citations
0
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: April 4, 2025
An efficient and expeditious method to assemble oxa-bridged polycycles bearing up six contiguous stereocenters from a gold(I)-catalyzed [3 + 2] cycloaddition/unactivated C(sp3)-H bond insertion cascade of o-1,6-enynyl benzaldehydes at low catalyst loading 2 mol % is described.
Language: Английский
Citations
0
The Chemical Record, Journal Year: 2025, Volume and Issue: unknown
Published: April 7, 2025
Abstract Gold catalysis has experienced remarkable progress over the past two decades, particularly in transformations involving alkynes. While numerous aspects of gold‐catalyzed reactions have been extensively reviewed, specific area cascade annulations between functionalized amines and alkynes represents a distinct rapidly developing direction that warrants focused attention. This survey collects systematically analyzes these transformations, which emerged as convenient synthetic strategies to diverse nitrogen heterocycles. The relevant are classified firstly by chemical nature amine functional substituent, secondly size formed ring. field under consideration bridges several fundamental practical branches chemistry, including catalysis, organic synthesis, medicinal materials science.
Language: Английский
Citations
0
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(4), P. 780 - 789
Published: Jan. 5, 2024
Abstract The functional group compatibility of our recently disclosed gold(I)‐catalyzed cycloisomerization 1‐bromoalkynes is studied in detail. Two main features are addressed, the minimum distances at which polar groups tolerated and influence both electronic steric effects on performance aryl ether derivatives. Moreover, robustness assessment experiments have been carried out shedding light factors dictating tolerance. In addition, reaction has applied to synthesis a key intermediate total natural product heterobifunctional molecule. DFT calculations shed mechanistic behind observed reactivity trends. On one hand, destabilization TS by proximity may hamper for proximal groups. other some not regardless their position due preferential coordination gold oxygen atom over alkyne, resulting presumably competitive catalyst deactivation pathways.
Language: Английский
Citations
3
Organic Letters, Journal Year: 2024, Volume and Issue: 26(13), P. 2635 - 2640
Published: March 25, 2024
A synthetic method for the efficient preparation of partially hydrogenated benzo[f]cyclobuta[cd]cyclopenta[h]benzofurans and cyclopropa[c]chromen-3a(1H)-ols that relies on gold(I)-catalyzed cascade cycloisomerization 3-allyloxy-1,6-diynes is described.
Language: Английский
Citations
3
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8734 - 8744
Published: May 30, 2024
A gold-catalyzed oxidative rearrangement of propargyl alcohols, derived from commercially available cyclohex-2-en-1-ones and alkynes, was successfully developed for the efficient synthesis seven-membered rings. Thorough investigations were conducted to optimize reaction conditions evaluate its compatibility with various functional groups. Additionally, this methodology applied formal total guanacastepene A, demonstrating practical utility in complex natural product synthesis. This versatile approach opens up new possibilities construction diverse ring systems, providing valuable building blocks further exploration drug discovery intricate molecules.
Language: Английский
Citations
2