Regio‐, and Stereoselective Iodobromination of Ynamides for Synthesis of (E)‐1‐Bromo‐2‐iodoenamides. Issue 15 (9th April 2014)

• Record Type: Journal Article
• Authors: Ide, Masataka; Yauchi, Yuta; Iwasawa, Tetsuo
• Is Part Of: European journal of organic chemistry. Issue 15(2014)
• Page Start: 3262
• Page End: 3267
• Publication Date: 2014-04-09
• Subjects: Synthetic methods -- Regioselectivity -- Alkynes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402057
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: One‐step synthesis of vicinal bromoiodoenamides from ynamides through IBr addition is described. Two types of IBr were used: commercially available IBr, and in situ generated IBr. This simple protocol enables highly efficient regio‐ and stereoselective iodobromination of the triple bond on a gram scale in anti ‐mode, and provides a potentially diverse scaffold for preparation of tetrasubstituted olefins. Abstract : Highly regio‐, and stereoselective addition reactions of IBr to ynamide were achieved by using either commercially available and/or in situ generated IBr. The method results in a single ( E )‐isomer product, and provides general entry to potentially diverse 1‐bromo‐2‐iodoenamide scaffolds bearing carbamate, indole, and benzyl tosylamide.