Organocatalyzed [4+2] Annulation of All‐Carbon Tetrasubstituted Alkenes with Allenoates: Synthesis of Highly Functionalized 2H‐ and 4H‐Pyran Derivatives. Issue 17 (20th October 2016)

• Record Type: Journal Article
• Authors: Ngo, Thi‐Thuy‐Duong; Kishi, Kenta; Sako, Makoto; Shigenobu, Masashi; Bournaud, Chloée; Toffano, Martial; Guillot, Régis; Baltaze, Jean‐Pierre; Takizawa, Shinobu; Sasai, Hiroaki; Vo‐Thanh, Giang
• Is Part Of: ChemistrySelect. Volume 1:Issue 17(2016)
• Page Start: 5414
• Page End: 5420
• Publication Date: 2016-10-20
• Subjects: References; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201601204
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A stereoselective [4+2] annulation of acyclic all‐carbon tetrasubstituted alkenes with allenoates was described. The reaction with DABCO proceeded smoothly leading to the formation of highly functionalized 4 H ‐pyran derivatives in good yields. We have also reported first β ‐ICD‐catalyzed [4+2] annulation affording functionalized enantioenriched 2H ‐pyran derivatives bearing a chiral all‐carbon quaternary center. Abstract : First amine‐catalyzed [4+2] annulation of ethyl allenoate and all‐carbon tetrasubstituted alkenes was described. Our finding procedure afforded the highly functionalized 2H ‐ and 4H ‐pyran derivatives bearing an all‐carbon quaternary center.