A new method for the synthesis of(R,R)-1,2-bis[(dimethoxyphenyl)phenylphosphino]ethane
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摘要:
以苯基二氯化膦为基础原料,经与甲醇反应后发生阿布佐夫重排得到甲基苯基亚膦酸酯,然后与五氯化膦反应生成甲基苯基膦酰氯;甲基苯基膦酰氯与手性辅助试剂5反应,然后再与2-甲氧基苯基溴化镁反应生成具有单一构型的(S)-(2-甲氧基苯基)甲基苯基氧化膦.膦氧化物7经二异丙基氨基锂(LDA)锂化,再通过氯化铜偶联,最后与三氯硅烷和三丁胺反应以89.5%收率和98.3/1.7 dr值(两个非对映异构体的比值)得到目标产物(R,R)-1,2-双[(2-甲氧基苯基)苯基膦]乙烷.
A new method for the synthesis of（R,R）-1,2-bis[（2-methoxyphenyl）phenylphosphino]ethane was developed.Basing on the reaction of Arbuzov rearrangement,methyl methylphenylphosphinate,which was obtained from dichlorophenylphosphine and methyl alcohol,reacted with phosphorus pentachloride to form methylphenylphosphinic chloride.Methylphenylphosphinic chloride successively reacted with oxazolidinone 5 and then with 2-methoxyphenylmagnesiumbromide to get（S）-（2-methoxypheny）methylphenylphosphine oxide as a single configuration.PAMPO 7 was coupled by the action of LDA and copper chloride,and then reduced with trichlorosilane and tributylamine to obtain target product with 89.5% yield and 98.3/1.7 dr value.
作者:
孙雨安 李宁 陈辉 张银龙 黄晓娜 李振兴 杨瑞娜
Sun Yuan;Li Ning;Chen Hui;Zhang Yinlong;Huang Xiaona;Li Zhenxing;Yang Ruina(College of Materials and Chemical Engineering,Zhengzhou University of Light Industry,Zhengzhou 450001,China;Institute of Chemistry,Henan Academy of Sciences,Zhengzhou 450002,China)
机构地区:
郑州轻工业学院材料与化学工程学院 河南省科学院化学研究所有限公司
出处:
《betway官方app 学报：自然科学版》 CAS 北大核心 2018年第5期56-60,共5页
基金:
国家自然科学基金(21502045) 河南省科技创新杰出青年基金(174100510018) 河南省科技开放合作项目(182106000015 17210600063)
关键词:
(R,R)-1,2-双[(2-甲氧基苯基)苯基膦]乙烷 合成 手性辅助试剂 甲基苯基膦酰氯
（ R,R ）-1,2-Bis［（dimethoxyphenyl）phenylphosphino］ethane synthesis chiral auxiliary reagent methylphenylphosphinic chloride
分类号:
O627.51 [理学—有机化学]
