A Mild Synthesis of Bicyclic Alkoxyoxazolium Salts from Proline and Pipecolic Acid Derivatives. Issue 31 (8th August 2019)

• Record Type: Journal Article
• Authors: Spinozzi, Eleonora; Bauer, Adriano; Maulide, Nuno
• Is Part Of: European journal of organic chemistry. Issue 31/32(2019)
• Page Start: 5230
• Page End: 5233
• Publication Date: 2019-08-08
• Subjects: Amide activation -- Oxazolium -- Chemoselectivity -- Cycloaddition -- Synthesis design; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201900985
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A regio‐ and chemoselective preparation of bicyclic alkoxyoxazolium salts from amide derivatives of proline and pipecolic acid by electrophilic amide activation is reported. Mechanistic NMR experiments suggest an unusual role for the base and highlight the effect of substitution pattern of the substrates. Abstract : All about no base: A regio‐ and chemoselective preparation of bicyclic alkoxyoxazolium salts from amide derivatives of proline and pipecolic acid by electrophilic amide activation is reported. Mechanistic NMR experiments suggest an unusual role for the base and highlight the effect of substitution pattern of the substrates.