| 词条 | Phosphoramidite |
| 释义 |
A phosphoramidite (RO)2PNR2 is a monoamide of a phosphite diester. The key feature of phosphoramidites is their markedly high reactivity towards nucleophiles catalyzed by weak acids e.c., triethylammonium chloride or 1H-tetrazole. In these reactions, the incoming nucleophile replaces the NR2 moiety. ApplicationsNucleoside phosphoramidites{{main|Nucleoside phosphoramidite}}Phosphoramidites derived from protected nucleosides are referred to as nucleoside phosphoramidites and are widely used in chemical synthesis of DNA, RNA, and other nucleic acids and their analogs. As ligands{{main|Phosphoramidite ligand}}Certain phosphoramidites are also used as monodentate chiral ligands in asymmetric synthesis.[1] A large group of such ligands is derived from the chiral diol BINOL and can be synthesis by reaction of BINOL with phosphorus trichloride to the chlorophosphite and then reaction with simple secondary amines.[2] This type of ligand was first used in 1996 in an asymmetric copper-catalysed addition of dialkylzincs to enones [3][4] See also
References1. ^{{Cite journal| doi = 10.1002/anie.200904948| pmid = 20333685| year = 2010| last1 = Teichert | first1 = J.| last2 = Feringa | first2 = B.| title = Phosphoramidites: Privileged Ligands in Asymmetric Catalysis.| volume = 49| issue = 14| pages = 2486–2528| journal = Angewandte Chemie International Edition in English }} {{organophosphorus}}2. ^{{Cite journal| doi = 10.1016/0957-4166(94)80032-4| title = α-Phenylethylamine based chiral phospholidines; new agents for the determination of the enantiomeric excess of chiral alcohols, amines and thiols by means of 31P NMR | first3 = B. L.| last3 = Feringa | first2 = N. K.| year = 1994| last2 = De Vries| last1 = Hulst | first1 = R.| journal = Tetrahedron: Asymmetry| volume = 5| issue = 4| pages = 699–708}} 3. ^{{Cite journal| doi = 10.1002/anie.199623741| title = Enantioselective Conjugate Addition of Dialkylzinc Reagents to Cyclic and Acyclic Enones Catalyzed by Chiral Copper Complexes of New Phosphorus Amidites| year = 1996| last1 = De Vries | first1 = A. H. M.| last2 = Meetsma | first2 = A.| last3 = Feringa | first3 = B. L.| journal = Angewandte Chemie International Edition in English| volume = 35| issue = 20| pages = 2374 }} 4. ^{{Cite journal| doi = 10.1002/anie.199726201| title = Highly Enantioselective Catalytic Conjugate Addition and Tandem Conjugate Addition–Aldol Reactions of Organozinc Reagents| year = 1997| last1 = Feringa | first1 = B. L.| last2 = Pineschi | first2 = M.| last3 = Arnold | first3 = L. A.| last4 = Imbos | first4 = R.| last5 = De Vries | first5 = A. H. M.| journal = Angewandte Chemie International Edition in English| volume = 36| issue = 23| pages = 2620 }} 2 : Phosphoramidites|Functional groups |
| 随便看 |
|
开放百科全书收录14589846条英语、德语、日语等多语种百科知识，基本涵盖了大多数领域的百科知识，是一部内容自由、开放的电子版国际百科全书。