134403-91-1Relevant academic research and scientific papers
Chemoselective Cleavage of Si-C(sp3) Bonds in Unactivated Tetraalkylsilanes Using Iodine Tris(trifluoroacetate)
Matsuoka, Keitaro,Komami, Narumi,Kojima, Masahiro,Mita, Tsuyoshi,Suzuki, Kimichi,Maeda, Satoshi,Yoshino, Tatsuhiko,Matsunaga, Shigeki
, p. 103 - 108 (2021/01/13)
Organosilanes are synthetically useful reagents and precursors in organic chemistry. However, the typical inertness of unactivated Si-C(sp3) bonds under conventional reaction conditions has hampered the application of simple tetraalkylsilanes in organic synthesis. Herein we report the chemoselective cleavage of Si-C(sp3) bonds of unactivated tetraalkylsilanes using iodine tris(trifluoroacetate). The reaction proceeds smoothly under mild conditions (-50 °C to room temperature) and tolerates various polar functional groups, thus enabling subsequent Tamao-Fleming oxidation to provide the corresponding alcohols. NMR experiments and density functional theory calculations on the reaction indicate that the transfer of alkyl groups from Si to the I(III) center and the formation of the Si-O bond proceed concertedly to afford an alkyl-λ3-iodane and silyl trifluoroacetate. The developed method enables the use of unactivated tetraalkylsilanes as highly stable synthetic precursors.
Enantioselective Copper-Catalyzed Intramolecular N?H Bond Insertion: Synthesis of Chiral 2-Carboxytetrahydroquinolines
Song, Xiao-Guang,Ren, Yuan-Yuan,Zhu, Shou-Fei,Zhou, Qi-Lin
, p. 2366 - 2370 (2016/08/16)
The first highly enantioselective intramolecular N?H bond insertion was realized by using copper catalysts modified with chiral spirobisoxazoline ligands, which provides a novel strategy for the synthesis of chiral 2-carboxytetrahydroquinolines. This reaction features fast reaction rate, high yield, high enantioselectivity, and mild reaction conditions. (Figure presented.).
A synthetic procedure for the preparation of oligonucleotides without using ammonia and its application for the synthesis of oligonucleotides containing O-4-alkyl thymidines
Eritja,Robles,Avino,Albericio,Pedroso
, p. 4171 - 4182 (2007/10/02)
The preparation of 5'-O-dimethoxytrityl (DMT) and p-nitrophenylethyl (NPEOC, NPE) protected nucleosides linked to 4-(2-hydroxyethyl)-3-nitrobenzoic acid derivatives is described. These products attached to controlled-pore glass supports and together with
NPE-resin, a new approach to the solid-phase synthesis of protected peptides and oligonucleotides I: Synthesis of the supports and their application to oligonucleotide synthesis
Eritja,Robles,Fernandez-Forner,Albericio,Giralt,Pedroso
, p. 1511 - 1514 (2007/10/02)
The preparation of polymeric supports containing a base labile 2-(2-nitrophenyl) ethyl linkage and the attachment of protected nucleosides is described together with their application to oligonucleotide synthesis.
