Transition metal-free aerobic oxidative cleavage of the C–N bonds of α-amino esters. Issue 23 (21st October 2019)

• Record Type: Journal Article
• Authors: Tan, Shenpeng; Li, Feng; Park, Soojun; Kim, Sanghee
• Is Part Of: Organic chemistry frontiers. Volume 6:Issue 23(2019)
• Page Start: 3854
• Page End: 3858
• Publication Date: 2019-10-21
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c9qo01033e
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A base-mediated aerobic oxidative cleavage of α-amino esters involving a hydroperoxide intermediate was reported, which represents the first example of the cleavage of the α-C–N bonds of amino acid derivatives without the aid of metal catalysts. Abstract : An efficient transition metal-free cleavage of the C–N bonds of α-amino esters under mild conditions has been developed. The reaction was performed in the presence of KO t Bu and molecular oxygen. Mechanistic studies reveal that the reaction proceeds through a base-mediated aerobic oxidative cleavage pathway involving the formation of a hydroperoxide intermediate.