Efficient and Direct Synthesis of γ‐Amino‐α, β‐Unsaturated Amides by Catalyzed Allylic Substitution of α‐Fluoroenamides: Toward to Synthesis of Hybrid Peptides and Indolizidines. Issue 12 (26th March 2018)

• Record Type: Journal Article
• Authors: Reddy, K. Harsha vardhan; Bédier, Matthieu; Bouzbouz, Samir
• Is Part Of: European journal of organic chemistry. Issue 12(2018)
• Page Start: 1455
• Page End: 1459
• Publication Date: 2018-03-26
• Subjects: Fluorenamides -- Indolizidines -- γ‐Amino‐α, β‐unsaturated amide -- Tripeptide -- Coniceine; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201800110
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A variety of γ‐amino‐α, β‐unsaturated amides have been synthesized from readily available α‐fluoroenamides precursors via an unprecedented intermolecular and intramolecular conjugative catalytic amination process. These γ‐amino‐α, β‐unsaturated amides are useful intermediates for accessing rarely synthesized hybrid peptides, αγα sequences, and various classes of alkaloids containing a pyrrolidine ring, as illustrated by total synthesis of the indolizidine alkaloid coniceine. Abstract : An intermolecular and intramolecular Pt‐catalyzed allylic amination process was developed for direct access of γ‐amino‐α, β‐unsaturated amides from α‐fluoroenamides. The utility of this transformation has been highlighted via the rapid and efficient synthesis of hybrids peptides and naturals products