Asymmetric hydroalkylation of alkynes and allenes with imidazolidinone derivatives: α-alkenylation of α-amino acids. Issue 21 (26th April 2021)

• Record Type: Journal Article
• Authors: Panahi, Farhad; Khosravi, Hormoz; Bauer, Felix; Breit, Bernhard
• Is Part Of: Chemical science. Volume 12:Issue 21(2021)
• Page Start: 7388
• Page End: 7392
• Publication Date: 2021-04-26
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1sc00240f
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Enantio-, diastereoselective, geometry-selective addition of imidazolidinone derivatives to alkynes and allenes in the presence of LiHMDS in order to obtain quaternary α-alkenyl substituted amino acids in high isolated yields. Abstract : This work reports a new method for the synthesis of quaternary α-alkenyl substituted amino acids by the enantio- and diastereoselective addition of imidazolidinone derivatives to alkynes and allenes. Further hydrolysis of the imidazolidinone products under acidic conditions afforded biologically relevant amino acid derivatives. This method is geometry-selective ( E -isomer), enantio- and diastereoselective, and products were obtained in good to excellent yields. The utility of this new methodology is proved by its operational simplicity and the successful accomplishment of gram-scale reactions. Experimental and computational studies suggest the key role of Li in terms of selectivity and support the proposed reaction mechanism.