偕双硅取代的手性α-氨基酸和β-氨基醇的不对称合成  

Asymmetric Synthesis of Geminal Bis(silyl)Chiralα-Amino Acid andβ-Amino Alcohol

作　　者：王润平 曹艳军 高璐[1] 宋振雷[1] WANG Run-ping;CAO Yan-jun;GAO Lu;SONG Zhen-lei(West China School of Pharmacy, Sichuan University, Chengdu 610041, China)

机构地区：[1]四川大学华西药学院,四川成都610041

出　　处：《合成化学》2021年第4期279-284,共6页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金优青项目(21622202)。

摘　　要：以3,3-偕双硅醛和(S)-叔丁基亚磺酰胺为原料,经7步反应,以20.2%和29.5%的收率合成了偕双硅α-氨基酸(12)和偕双硅β-氨基醇(14)。其中,14可进一步以50%的收率转化为相应的手性单噁唑啉配体(15),产物结构经^(1)H NMR,^(13)C NMR和HR-MS(ESI)表征,绝对构型经XRD确证,光学纯度由HPLC手性OD柱测定。Gemianl bis(silyl)α-amino acid(12)andβ-amino alcohol(14)were synthesized by a seven-step reaction with overall yields of 20.2%and 29.5%,respectively,from 3,3-geminal bis(triethylsilyl)aldehyde and(S)-tert-butylsulfonamide.Geminal bis(silyl)β-amino alcohol(14)was further converted into the corresponding chiral mono-oxazoline ligand 15 in 50%yield.The structures of the products were characterized by ^(1)H NMR,^(13)C NMR and HR-MS(ESI).The absolute configuration was confirmed by X-ray diffraction spectrum and the optical purity was determined by HPLC Chiralpak OD column.

关 键 词：偕双硅 Α-氨基酸 Β-氨基醇 叔丁基亚磺酰胺 配体 合成 构型 光学纯度 

分 类 号：O62[理学—有机化学]