文献类型：期刊文献

英文题名：Asymmetric aza-Morita-Baylis-Hillman reaction of N-sulfonated imines with methyl vinyl ketone catalyzed by chiral phosphine Lewis bases bearing perfluoroalkanes as "pony tails"

作者：Shi, M; Chen, LH; Teng, WD

机构：[1]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China;[2]E China Univ Sci & Technol, Sch Chem & Pharmaceut, Shanghai 200237, Peoples R China

年份：2005

卷号：347

期号：14

起止页码：1781

外文期刊名：ADVANCED SYNTHESIS & CATALYSIS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000233483000009)，CCR-EXPANDED(收录号:WOS:000233483000009)】；

语种：英文

外文关键词：asymmetric organic catalysis; aza-Morita-Baylis-Hillman reaction; chiral phosphine Lewis base; methyl vinyl ketone; perfluoroalkane chain; N-sulfonated imines

摘要：In the aza-Morita-Baylis-Hillman reaction of N-sulfonated imines (N-arylmethylidene-4-methyl-benzenesulfonamides and others) with methyl vinyl ketone (MVK), we found that in the presence of a catalytic amount of the chiral phosphine Lewis bases (R)-(-)-6,6 '-bis[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tri-decafluorooctyl)silyl]-2 '-(diphenylphosphanyl)-[1,1 ' 1- binaphthalenyl-2-ol LB2 and (R)-(-)-6,6 '-(3,3,4,4,5, 5,6,6,7,7,8,8,8-tridecafluorooctyl) -2 '-(diphenylphosphanyl)-[1,1 ']binaphthalenyl-2-ol LB3 bearing two perfluoroalkane chains at 6,6 '-positions of the naphthalene framework, the corresponding adducts could be obtained in good yields with good to high ee (52-95% ee) at room temperature (15 degrees C or low temperature (-20 degrees C) in THF, respectively. LB3 is more effective in this reaction than the previously reported original chiral phosphine Lewis base (R)-(-)2 '-diphenylphosphanyl-[1,1 ']binaphthalenyl-2-ol LB1.