2-(N-三氟乙酰-N-三甲基硅烷基)氨基-3-三甲基硅烷氧基-羧酸三甲基硅烷酯和2-(N-三氟乙酰)-2,3-脱氢氨基酸的合成

Syntheses of Trimethylsilyl 2-(N-trifluoroacetyl-N-trimethylsilyl) amino-3-trimethylsiloxyl Carboxylates and N-Trifluoroacetyl-2, 3-didehydroamino Acids

近十几年来,N原子上带有保护基团的α,β脱氢氨基酸及其衍生物的新的合成方法,由于发现这类化合物存在于微生物、低等植物和海生动物体中而具有重要意义。

This paper describes the syntheses of 2-(N-trifluoroacetylamino-N-trimethyl-silyl)1,1-bis(trimethylsiloxy) ethene (3), trimethylsilyl 2-(N-trifluoroacetyl-N-trimethylsilyl) amino-3-(trimethylsiloxy) carboxylates (5) and N-trifluoroacetyldidehydroamino acids (6). N-tri-fluoroacetyl-glycine is silylated by trimethylsilyl triflate (2) in the presence of triethylamineto yield 3. Reaction of aliphatic and aromatic aldehydes 4 with 3 under the catalysis ofzinc bromide affords 5. Elimination of trimethylsilanol from 5 by using trifluoromethansul-fonic acid or 2 and treating the reaction mixture with saturated ammonium chloride solutionthen yield 6.