α-Nitrogenated organolithium compounds from α-amidomethyl and α-aminomethyl sulfones
作者:Diego A. Alonso、Emma Alonso、Carmen Nájera、Diego J. Ramón、Miguel Yus
DOI:10.1016/s0040-4020(97)00166-x
日期:1997.3
methylenated to the corresponding acyl enamines 16 or 17 with in situ generated chloromethylmagnesium chloride. Naphthalene-catalysed lithiation of α-aminomethyl sulfone 19 in the presence of electrophiles [ButCHO, PhCHO, Et2CO, Pr2iCO, (CH2)5CO, PhCOMe] at −78 to 0°C leads, after hydrolysis with water, to the expected aminoalcohols 20. The application of this method to α-amidomethyl sulfones 7c,d using
的连续反应α-酰氨基甲基砜7A,7B,从伯酰胺衍生的,具有Ñ丁基锂和伯烷基溴化物(CH 2 CHCH 2 BR,CH 2 CMeCH 2 BR,CH 2 CBrCH 2 BR,CHCCH 2 BR,物理信道2 BR,卜吨ö 2 CCH 2 BR)在-90℃下的产率,水解后,烯酰胺11。相同的步骤适用于衍生自仲酰胺并使用不同亲电试剂的α-酰胺基甲基砜7c,d [AcOD,D 2 O,EtI,CH 2 = CHCH2 BR,卜Ñ I,的PhCH 2 BR,卜吨ö 2 CCH 2 BR,卜吨CHO,苯甲醛,(CH 2)4 CO,EtOCOCl,CH 3氯化钴,PhCOCl]给出取代的α-酰氨基甲基砜13。将代表性化合物13脱磺化(Na·Hg,Na 2 S 2 O 4或Mg-MeOH),得到酰胺15。锂化砜13被methylenated到相应的酰基烯胺16或17与在原位生成氯甲基氯化镁。萘