Methyltrioxorhenium/urea hydrogen peroxide catalyzed oxidation of N-sulfinyl imines: A mild and highly efficient access to N-sulfonyl aldimines, ketimines and α-ketiminoesters. Issue 51 (17th December 2020)

• Record Type: Journal Article
• Authors: Tan, Yu; Ma, Ru-Lin; Lin, Hua; Sun, Xing-Wen
• Is Part Of: Tetrahedron letters. Volume 61:Issue 51(2020)
• Publication Date: 2020-12-17
• Subjects: Methyltrioxorhenium -- Urea hydrogen peroxide -- N-Sulfinyl imines -- N-Sulfonyl imines -- Quaternary α-amino acids; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152587
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Synthesis of N -sulfonyl imines by the oxidation of N- sulfinyl imines using MTO/UHP. The unstable sulfonylimines. Synthesis of quaternary α -amino acids via allylation of α -ketiminoesters. Abstract: A mild and highly efficient access to N -sulfonyl imines through the oxidation of corresponding N - tert -butylsulfinyl imines and N - p -tosyl-sulfinyl imines with UHP in the presence of catalytic amount MTO was developed. Under mild reaction conditions, this highly selective reaction, provides a general and efficient access to N -sulfonyl aldimines, ketimines and α -ketiminoesters in excellent yield. The unstable sulfonylimine intermediates can be afforded with high purity and ready for subsequent reaction without further purification. The application of this method was demonstrated by facile synthesis of quaternary α -amino acids derivatives via allylation of obtained α -ketiminoesters.