Enantioselective Synthesis of 4H‐Pyrans Through Organocatalytic Asymmetric Formal [3+3] Cycloadditions of 2‐(1‐Alkynyl)‐2‐alken‐1‐ones with β‐Keto Esters. Issue 19 (24th August 2016)

• Record Type: Journal Article
• Authors: Yue, Zhenting; Li, Wenbo; Liu, Lu; Wang, Cuihong; Zhang, Junliang
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 19(2016)
• Page Start: 3015
• Page End: 3020
• Publication Date: 2016-08-24
• Subjects: bifunctional catalysts -- [3+3] cycloaddition -- eco-friendly reactions -- enantioselectivities -- 4H-pyrans; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600591
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 4 H ‐Pyran units are frequently present in molecules with significant biological and pharmaceutical activities. Herein, we present the first enantioselective formal [3+3] cycloaddition between 2‐(1‐alkynyl)‐2‐alken‐1‐ones and β‐keto esters catalyzed by a cyclohexyldiamine‐based thiourea‐tertiary amine bifunctional catalyst. Under the mild and eco‐friendly conditions, a wide range of polysubstituted 4 H ‐pyrans were obtained in moderate yields with good enantioselectivities. Abstract :