Base‐Catalyzed Intramolecular 5‐exo‐dig Cyclization of 2‐Propynyl‐1, 3‐dicarbonyl Compounds: An Atom‐Economic Route to Stereodefined 2‐Methylene‐2, 3‐dihydrofurans. Issue 23 (7th July 2014)

• Record Type: Journal Article
• Authors: Ma, Quan; Wang, Yeming; Zhao, Yuegang; Liao, Peiqiu; Sun, Bo; Bi, Xihe
• Is Part Of: European journal of organic chemistry. Issue 23(2014)
• Page Start: 4999
• Page End: 5003
• Publication Date: 2014-07-07
• Subjects: Oxygen heterocycles -- Spiro compounds -- Alkynes -- Cyclization -- Intramolecular reactions -- Base catalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402542
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A new and straightforward base‐catalyzed 5‐ exo ‐ trig cyclization of 2‐propynyl‐1, 3‐dicarbonyl compounds leads to the corresponding stereodefined 2‐methylene‐2, 3‐dihydrofurans in excellent yields. Abstract : A regio‐ and stereoselective 5‐ exo ‐ dig cyclization of 2‐propynyl‐1, 3‐dicarbonyl compounds under metal‐free conditions has been developed. This reaction constitutes a new and straightforward method for the efficient synthesis of stereodefined 2‐methylene‐2, 3‐dihydrofurans. Spiro‐dihydrofurans can also be prepared in excellent yields by this approach.