Synthesis of Quaternary α-Fluorinated α-Amino Acid Derivatives via Coordinating Cu(II) Catalytic α-C(sp3)–H Direct Fluorination

• DOI: 10.1021/acs.orglett.8b03044
• Publication Date: 2018-10-26T15:51:38Z
• Authors: Qiang Wei; Yao Ma; Li Li; Qingfei Liu; Zijie Liu; Gang Liu
• Keywords: 01 natural sciences; 0104 chemical sciences

A coordinating, copper-catalyzed direct α-C(sp3)–H fluorination method has been developed to prepare vital quaternary α-fluorinated α-amino acid derivatives. Cu(II) catalytic SET oxidative addition mechanism is proposed, involving a key fluoride-coupled charge transfer complex. The protocol can tolerate rich variety of acids, for which the auxiliary group removed in high yield and substituted preparation dipeptide derivatives with detachable, single absolute configurations target compounds.