Anti-Selective synthesis of β-boryl-α-amino acid derivatives by Cu-catalysed borylamination of α, β-unsaturated esters. Issue 48 (30th November 2022)

• Record Type: Journal Article
• Authors: Nishino, Soshi; Nishii, Yuji; Hirano, Koji
• Is Part Of: Chemical science. Volume 13:Issue 48(2022)
• Page Start: 14387
• Page End: 14394
• Publication Date: 2022-11-30
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2sc06003e
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A Cu-catalysed regio-, diastereo-, and enantioselective borylamination of α, β-unsaturated esters with B2 pin2 and hydroxylamines has been developed. The products can be converted into functionalised α-amino acids with two adjacent stereocentres. Abstract : A copper-catalysed regio- and diastereoselective borylamination of α, β-unsaturated esters with B2 pin2 and hydroxylamines has been developed to deliver acyclic β-boryl-α-amino acid derivatives with high anti -diastereoselectivity (up to >99 : 1), which is difficult to obtain by the established methods. A chiral phosphoramidite ligand also successfully induces the enantioselectivity, giving the optically active β-borylated α-amino acids. The products can be stereospecifically transformed into β-functionalised α-amino acids, which are of potent interest in medicinal chemistry.