This approach, catalyzed by Rh(III), is combined with the α-arylation of ketone-derived silyl enol ethers to achieve a direct cross-coupling event. If the reaction were controlled solely by thermodynamics then, statistically, if the dianion is of similar reactivity to the monoanion, then a corresponding statistical mixture of 1:2:1 disilylated:monosilylated:unsilylated diol will result. If you have the appropriate software installed, you can download article citation data to the citation manager of your choice. 2, has been elucidated by X-ray analysis. [1] If DMF is replaced by dichloromethane, the reaction is somewhat slower, but the purification of the compound is simplified. Please enable JavaScript Purification involves the addition of an aqueous acid such as saturated ammonium chloride solution. Synthesis and conformational analysis of 2-arylseleno-1,3-dithianes. Corey, E. J.; Venkateswarlu, A. Silyl triflates are water sensitive and must be run under inert atmosphere conditions. Journal of the American Chemical Society 2003 , 125 (1) , … [2] Primary alcohols can be protected in less than one hour while some hindered alcohols may require days of reaction time. XX is the XXth reference in the list of references. ; Condon, B. D. "A convenient procedure for the monosilylation of symmetric 1, Roush, W. R.; Gillis, H. R.; Essenfeld, A. P. "Hydrofluoric acid catalyzed intramolecular Diels-Alder reactions ". If you are the author of this article you do not need to formally request permission Reaction with acids or fluorides such as tetra-n-butylammonium fluoride removes the silyl group when protection is no longer needed. At the initial addition of TBSCl, there is only a minor amount of monoanion in solution with the rest being in suspension. The Crystallographic Structure of a Lewis Acid-Assisted Chiral Brønsted Acid as an Enantioselective Protonation Reagent for Silyl Enol Ethers. Hu, L.; Liu, B.; Yu, C. Tetrahedron Lett. In all cases the Ref. The one-electron oxidation with 2 equivalents of [Fe(phen)3](PF6)3 furnished in all three cases 3-mesityl-4,6,7-trimethyl-2-phenylbenzofuran 4 in high yield. or in a thesis or dissertation provided that the correct acknowledgement is given This page was last edited on 5 March 2019, at 11:19. "First total synthesis of taxol. to access the full features of the site or access our, Instructions for using Copyright Clearance Center page. Holton, R. A. et al. Check if you access through your login credentials or your institution to get full access on this article. If excess reagent is used, the product will require flash chromatography to remove excess silanol and siloxane. Carbon–hydrogen (C–H) bond functionalization streamlines synthesis by increasing step- and atom-economies.

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