Enantioselective Rauhut−Currier Reactions Promoted by Protected Cysteine

2006/12/20 by Carrie E. Aroyan, Scott J. Miller · 2 citations
Chemistry · Biochemistry, Genetics and Molecular Biology · #Asymmetric Synthesis and Catalysis #Chemical Synthesis and Analysis #Synthetic Organic Chemistry Methods

paper · doi:10.1021/ja067139f

openalex publication_date 2006/12/20 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/15

Abstract

We report highly enantioselective examples of the Rauhut−Currier cycloisomerization reaction (the “vinylogous Morita−Baylis−Hillman reaction”). The reaction is highly practical and is catalyzed by a commercially available derivative of the proteinogenic amino acid cysteine. Reactions are conducted in the presence of potassium tert -butoxide and a critical concentration of water in bulk acetonitrile. A mechanistic model is advanced that may account for reaction selectivity that is predicated on organizational chelation of K ion in the product-determining step in which the Cys derivative undergoes elimination.

Citations

• Organocatalytic Michael Cycloisomerization of Bis(enones): The Intramolecular Rauhut−Currier Reaction
• The Vinylogous Intramolecular Morita−Baylis−Hillman Reaction: Synthesis of Functionalized Cyclopentenes and Cyclohexenes with Trialkylphosphines as Nucleophilic Catalysts

Cited by

• Recent Contributions from the Baylis−Hillman Reaction to Organic Chemistry
• Rauhut–Currier reaction [wikipedia]