Mechanochemically performed boronation of arene diazonium salts is presented. The key feature of this method is NaCl which significantly enhances this procedure. Mechanistic and DFT investigations suggest plausible mechanism and action of chlorid...
Artikel
Stereoselective Synthesis of Glycosyl Cyanides by TMSOTf‐Mediated Ring Opening of 1,6‐Anhydro Sugars
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The stereocontrolled TMSOTf-ring opening of 1,6-anhydrosugars with TMSCN leading to glycosyl cyanides is presented as well as an application to the straightforward synthesis of a conformationally-constrained analogue of 1-cyano D-glucal.
Abstract
We describe herein a convenient access to glycosyl cyanides by way of TMSCN ring opening of 1,6-anhydro sugars mediated by TMSOTf with modest to high stereocontrol in the D-gluco, D-galacto and D-manno series. The reaction is tolerant to various functional groups including free alcohols, alkenes and terminal alkynes. The straightforward synthesis of a constrained analogue of 1-cyano-D-glucal with a 3,6-anhydro sugar framework is presented to illustrate the interest of the TMSCN ring-opening reaction.
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