+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Gold(I)-Catalyzed Angle Strain Controlled Strategy to Furopyran Derivatives from Propargyl Vinyl Ethers: Insight into the Regioselectivity of Cycloisomerization



Gold(I)-Catalyzed Angle Strain Controlled Strategy to Furopyran Derivatives from Propargyl Vinyl Ethers: Insight into the Regioselectivity of Cycloisomerization



Organic Letters 18(4): 680-683



A unique strategy for the regiospecific synthesis of bicyclic furopyran derivatives has been developed via a gold(I)-catalyzed propargyl-Claisen rearrangement/6-endo-trig cyclization of propargyl vinyl ethers. The introduction of angle strain into the substrates significantly altered the reaction's regioselectivity. Insight into the regioselectivity of the cycloisomerization was obtained with density functional theory calculations.

Please choose payment method:






(PDF emailed within 0-6 h: $19.90)

Accession: 057949931

Download citation: RISBibTeXText

PMID: 26841301

DOI: 10.1021/acs.orglett.5b03641


Related references

A gold(i)-catalyzed substituent-controlled cycloisomerization of propargyl vinyl ethers to multi-substituted furofuran and furopyran derivatives. Chemical Communications 52(37): 6233-6236, 2016

Synthesis of Substituted 1,2-Dihydropyridines from Propargyl Vinyl Ethers and Allenic Vinyl Ethers by Gold-Catalyzed Claisen Rearrangement and 6-Aza-electrocyclization. Advanced Synthesis & Catalysis 352(14-15): 2450-2454, 2010

Mechanistic insights into the gold-catalyzed cycloisomerization of bromoallenyl ketones: ligand-controlled regioselectivity. Journal of the American Chemical Society 130(22): 6940-6941, 2008

Synthesis of Indenes by Tandem Gold(I)-Catalyzed Claisen Rearrangement/Hydroarylation Reaction of Propargyl Vinyl Ethers. Journal of Organic Chemistry 84(10): 6298-6311, 2019

Pentannulation Reaction by Tandem Gold(I)-Catalyzed Propargyl Claisen Rearrangement/Nazarov Cyclization of Enynyl Vinyl Ethers. Organic Letters 20(15): 4713-4717, 2018

Cobalt-catalyzed cycloisomerization of 1,6-enynes and allyl propargyl ethers. Organic Letters 5(14): 2409-2411, 2003

The facile synthesis of 1-benzoazepine derivatives via gold-catalyzed regioselective cycloisomerization reactions of N-(o-alkynylaryl)-N-vinyl sulfonamides. Chemical Communications 52(26): 4824-4827, 2016

Rhodium-catalyzed cycloisomerization of N-propargyl enamine derivatives. Journal of the American Chemical Society 128(19): 6336-6337, 2006

Theoretical Insight into the Mechansim and Origin of Ligand-Controlled Regioselectivity in Homogenous Gold-Catalyzed Intramolecular Hydroarylation of Alkynes. Journal of Organic Chemistry 83(5): 2763-2772, 2018

Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals. Organic Letters 18(5): 928-931, 2016

Gold-catalyzed cascade cycloisomerization of 1,7-diyn-3,6-bis(propargyl carbonate)s: stereoselective synthesis of naphtho[b]cyclobutenes. Chemical Communications 49(77): 8650-8652, 2013

Gold-catalyzed annulations of 2-alkynyl benzaldehydes with vinyl ethers: synthesis of dihydronaphthalene, isochromene, and bicyclo[2.2.2]octane derivatives. Chemistry 19(12): 4043-4050, 2013

Regioselectivity switch: gold(I)-catalyzed oxidative rearrangement of propargyl alcohols to 1,3-diketones. Journal of Organic Chemistry 77(17): 7761-7767, 2012

Stereocontrolled synthesis of (E,Z)-dienals via tandem Rh(I)-catalyzed rearrangement of propargyl vinyl ethers. Organic Letters 15(17): 4462-4465, 2013

Gold-Catalyzed Synthesis of Quinolines from Propargyl Silyl Ethers and Anthranils through the Umpolung of a Gold Carbene Carbon. Angewandte Chemie 55(41): 12688-12692, 2016