公开(公告)号：US20130137889A1

公开(公告)日：2013-05-30

申请号：US13702060

申请日：2010-03-26

申请人： Guigen Li ,  Xiangzhen Sun ,  Huabing Chen

发明人： Guigen Li ,  Xiangzhen Sun ,  Huabing Chen

IPC分类号： C07F9/6584 ,  C07F5/06 ,  C07F9/6574

CPC分类号： C07F9/65848 ,  C07F5/066 ,  C07F5/068 ,  C07F5/069 ,  C07F9/657154 ,  C07F9/65742

摘要： Strecker reagents, their derivatives and methods for forming the same and improved Strecker reaction are provided. The electrophiles for asymmetric Strecker reaction include achiral N-phosphorazides, N-phosphoramides, N-phosphonyl imines and their derivatives. The nucleophiles for asymmetric Strecker reaction include chiral BINOL-derived azides, amides, imines and their derivatives, the chiral and achiral diol-based cyanides and their derivatives, the chiral and achiral diamine-based cyanides and their derivatives, the chiral and achiral amino alcohol-based cyanides and their derivatives, the Strecker nucleophiles that are derived from chiral and achiral hydroxyl carboxylic acids and amino acids. Methods of forming the electrophile for asymmetric Strecker reaction comprise the reactions with steps of: a) synthesizing phosphoryl chloride from achiral diamine; b) synthesizing phosphorous azide; c) synthesizing phosphoramide; d) synthesizing the corresponding achiral N-phosphonyl imines. The asymmetric catalytic Strecker reaction of new achiral N-phosphonyl imines has been developed to give excellent enantioselectivity (up to >99% ee) and yields (up to >97%).

摘要翻译： 提供了Strecker试剂，其衍生物和形成相同和改进的Strecker反应的方法。 用于不对称Strecker反应的亲电子试剂包括非手性N-磷酰肼，N-磷酰胺，N-膦酰基亚胺及其衍生物。 用于不对称Strecker反应的亲核试剂包括手性BINOL衍生的叠氮化物，酰胺，亚胺及其衍生物，手性和非手性二醇基氰化物及其衍生物，手性和非手性二胺基氰化物及其衍生物，手性和非手性氨基醇 的氰化物及其衍生物，衍生自手性和非手性羟基羧酸和氨基酸的Strecker亲核体。 形成不对称Strecker反应的亲电子试剂的方法包括以下步骤的反应：a）从非手性二胺合成磷酰氯; b）合成磷叠氮化物; c）合成磷酰胺; d）合成相应的非手性N-膦酰基亚胺。 已经开发了新的非手性N-膦酰亚胺的不对称催化Strecker反应，以提供优异的对映选择性（高达> 99％ee）和产率（高达> 97％）。