Highly Selective Syn Addition of 1, 3‐Diones to Internal Ynamides Catalyzed by Zinc Iodide. Issue 11 (22nd March 2018)

• Record Type: Journal Article
• Authors: Plamont, Rémi; Graux, Lionel V.; Clavier, Hervé
• Is Part Of: European journal of organic chemistry. Issue 11(2018)
• Page Start: 1372
• Page End: 1376
• Publication Date: 2018-03-22
• Subjects: Hydroalkoxylation -- Homogeneous catalysis -- Regioselectivity -- Lewis acids -- Enamines; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701690
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 1, 3‐Diones are already established as nucleophiles to perform additions to ynamides; the highly selective hydroalkoxylation of internal ynamides is now described. Several catalytic systems have been compared to perform this transformation, including transition‐metal‐based catalysts and Lewis acids. ZnI2 was found to be both very active and highly selective providing only E adducts through a syn addition. Investigation of the scope and limitations showed that this catalyst was compatible with various functional groups. In addition to seventeen examples of ynamide hydroalkoxylation, one example of ynamide hydroarylation is reported. Abstract : The hydroalkoxylation of internal ynamides with 1, 3‐diones was achieved in a highly syn manner by using zinc iodide as a Lewis acid catalyst. The scope of this transformation was found to be broad and compatible with various functional groups.