Catalytic and metal-free intramolecular hydroalkoxylation of alkynes. Issue 7 (14th February 2019)

• Record Type: Journal Article
• Authors: Jean, Alexandre; Rouden, Jacques; Maddaluno, Jacques; De Paolis, Michaël; Blanchet, Jérôme
• Is Part Of: Tetrahedron letters. Volume 60:Issue 7(2019)
• Page Start: 534
• Page End: 537
• Publication Date: 2019-02-14
• Subjects: Hydroalkoxylation -- Cyclization -- Alkynes -- Enol ether -- Microwave-assisted synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.01.020
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Metal-free synthesis of exocyclic enol ethers. Simple catalyst and reaction conditions. Microwave assisted unusual hydroalkoxylation of linear alkynes. Fast and stereoselective process. Abstract: Benzyltrimethylammonium hydroxide act as an efficient metal-free catalyst for the intramolecular hydroalkoxylation of alkynes. Notably, the use of microwave irradiation allowed reaction to operate in only two minutes. Under optimized reaction conditions, linear alkynes bearing aryl and heteroaryl substituents were successfully cyclized with good level of stereoselectivity.