手性膦路易斯碱催化 N-磺酰亚胺与甲基乙烯基酮和苯基丙烯酸酯的不对称氮杂 Baylis-Hillman 反应。
Chiral phosphine Lewis base catalyzed asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines with methyl vinyl ketone and phenyl acrylate.
作者信息
Shi Min, Chen Lian-Hui
机构信息
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
出版信息
Chem Commun (Camb). 2003 Jun 7(11):1310-1. doi: 10.1039/b301863f.
In the aza-Baylis-Hillman reaction of N-sulfonated imines with methyl vinyl ketone (MVK) promoted by chiral phosphine Lewis base: (R)-2'-diphenylphosphanyl-[1,1']binaphthalenyl-2-ol (10 mol%), the aza-Baylis-Hillman adducts 1 were obtained in good yields with high ee (70-94% ee) at -30 degrees C in THF. In CH2Cl2 upon heating at 40 degrees C, the aza-Baylis-Hillman reaction of N-sulfonated imines with phenyl acrylate gave the adducts 2 in high yields (60-97%) with moderate ee (52-77%).
在手性膦路易斯碱（R）-2'-二苯基膦基-[1,1']联萘-2-醇（10 mol%）促进下，N-磺酰亚胺与甲基乙烯基酮（MVK）发生氮杂-Baylis-Hillman反应：在-30℃的四氢呋喃中，以高对映体过量（ee值为70 - 94%）高产率得到氮杂-Baylis-Hillman加合物1。在二氯甲烷中于40℃加热时，N-磺酰亚胺与丙烯酸苯酯的氮杂-Baylis-Hillman反应以中等对映体过量（ee值为52 - 77%）高产率（60 - 97%）得到加合物2。
Zotero 插件