Gold(I)−Catalyzed Synthesis of Cyclic Sulfamides via an Intramolecular Dehydrative Amination of Allylic Alcohols: A Strategy for 1,3-Diamine Synthesis

Soyun Lee, Da Mi Kim, Jae Sang Ryu

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

A gold(I)-catalyzed intramolecular dehydrative amination method has been developed to synthesize diverse cyclic sulfamides efficiently. Reactions proceed smoothly at room temperature using a combination of (IPr)AuCl (5 mol%) and AgBF4 (5 mol%). This method showcases a broad substrate scope, encompassing challenging seven-membered ring structures, and exhibits functional group compatibility. Moreover, the reaction demonstrates high stereoselectivity, allowing the synthesis of enantiomerically enriched cyclic sulfamides from chiral secondary allylic alcohols. The synthesized cyclic sulfamides serve as valuable intermediates for generating 1,3-diamines. This approach provides an improved route for cyclic sulfamide synthesis and a strategic entry point for obtaining essential 1,3-diamine derivatives.

Original languageEnglish
Pages (from-to)3379-3386
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume366
Issue number15
DOIs
StatePublished - 6 Aug 2024

Bibliographical note

Publisher Copyright:
© 2024 The Author(s). Advanced Synthesis & Catalysis published by Wiley-VCH GmbH.

Keywords

  • Amination
  • Cyclic sulfamide
  • Gold
  • Homogeneous catalysis
  • Silver

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