应用化学2018，Vol.35Issue(2)：189-196,8.DOI:10.11944/j.issn.1000-0518.2018.02.170066
手性芳基膦-噁唑啉的简便合成
A Facile Synthesis of Chiral Phosphinoaryloxazolines
摘要
Abstract
As a widely used class of privileged ligands,phosphinoaryloxazolines(PHOX)have attracted much attention from chemists.However,the previous synthetic methods have problems of long steps,low yield and difficult separation and so on.In this article, a simple and efficient procedure for the synthesis of phosphinoaryloxazolines(PHOX)has been developed.First, 2-(diphenylphosphino)benzoic acid was condensed with various enantiomerically pure amino alcohols in the presence of 1-hydroxylbenzotriazole (HOBt)and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride(EDCI)in dimethylformamide to give the corresponding(amido alcohol)s amides in excellent yields.Then the(amido alcohol)s amides were subjected to the oxazoline ring formation by treatment with triphenylphosphine, triethylamine and carbon tetrachloride in acetonitrile to afford a series of phosphinooxazolines in 64%~86%total yields.Subsequently, (S)-t-BuPHOX was applied in the palladium-catalyzed decarboxylative Tsuji allylations of β-ketoester,giving an excellent isolated yield of 80%with an enantiomeric excess of 84%.The new synthetic procedure has the advantages of using readily available starting materials,mild reaction conditions,and high overall yields.关键词
膦-噁唑啉配体/(二苯基膦基)苯甲酸/手性氨基醇Key words
phosphinooxazolines/(diphenyl-phosphino)benzoic acid/chiral amino alcohols分类
化学化工引用本文复制引用
曹宝辰,吴国杰,何宇鹏,韩福社..手性芳基膦-噁唑啉的简便合成[J].应用化学,2018,35(2):189-196,8.基金项目
国家自然科学基金资助项目(21602215) （21602215）
国家海洋局海洋生物资源综合利用工程技术研究中心开放基金课题(MBRCU201604)Supported by the National Natural Science Foundation of China(No.21602215),the Fund of the Engineering Research Center of Marine Bioresources Comprehensive Utilization,SOA(No.MBRCU201604) （MBRCU201604）
