Separations and Syntheses of Chiral Compounds and Application to the Synthesis of Natural Products using Fluorous Chemistry

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  • フルオラスケミストリーを用いるキラル化合物の分離・合成および天然物合成への利用
  • フルオラスケミストリー オ モチイル キラル カゴウブツ ノ ブンリ ゴウセイ オヨビ テンネンブツ ゴウセイ エ ノ リヨウ

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Abstract

Organic compounds that bear perfluoroalkyl substituents such as CH2CH2CnF2n+1 (n=4-10) and the fluorine atom contents of which are higher than 60 wt% are soluble in perfluorocarbon like FC-72 (CF3 (CF2) 4CF3) but insoluble in common organic solvents. The unique nature has been applied to a simple and quick separation of organic products from a fluorous reagent, or a fluorous product from organic reagents, and to immobilization of a fluorous catalyst in the fluorous phase of a fluorous and organic biphase system. Using a fluorous silica gel column, fluorous compounds that bear only a single fluorous substituent can easily be separated from organic compounds but also themselves can be separated by HPLC depending upon their fluorine atom contents. Here we describe catalytic enantioselective reactions using fluorous BINOL and BINAP in the biphase system, separation of enantiomers of fluorous chiral alcohols and α-amino acid derivatives by HPLC with a β-cyclodextrin chiral column and a total synthesis of macrolactam bistratamide H using a new fluorous protecting group, 2-tris (pefluorodesyl) silylethoxycarbonyl.

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