N-TMS-β,β-difluoroenamines: Electrochemical preparation and its transformation

✍ Scribed by Kenji Uneyama; Tsuyoshi Kato

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 204 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)10613-x

✦ Synopsis

The first prel~r~ion of N-tfimethylsilylated l~,~difluoroe~mines (2) from the trifluoromethyl imines (1) by deetrochemical reductionand a preliminary study on alkylation of 2 for the synthesis of difluoromethylene compounds are desa'ibed. @ 1998 Elsevier Science Ltd. All fights reserved.

~,[I-Difluoroamino acids are synthetic targets t which possess a potential biological activity and are relatively unexplored compounds. Constructions of the difluoromethylene moiety in the molecules are achieved by transformation of the carbonyl and thiocarbonyl groups by fluorinatng reagents, 2 substitution of two methylene protons with fluorine atoms by N-F reagents, 3 utilization of A typical procedure is as follows: Ethyl 2-(N-p-anisyl)imino-3,3,3-trifluoropropanoate (la) (1.0 mmol), TMSCI (3.0 mmol), triethylamine (3.2 mmol) and dry DMF (6.