A convenient multigram synthesis of highly enantioenriched methyl 3-silylglycidates

The Journal of Organic Chemistry
Jason T LoweJames S Panek

Abstract

A multigram scale synthesis of the four stereoisomers of methyl 3-silylglycidates (epoxysilanes) with high enantiopurity is described. Key reactions include a Sharpless asymmetric epoxidation (SAE) of a trans-vinylsilane and an enzymatic resolution of a racemic cis-epoxysilane to establish the desired configurations. Few chromatographic separations (5 columns out of 13 steps) are required for purification, establishing a convenient reaction sequence for both the trans- and cis-isomers.

References

Feb 19, 2002·Chemical Reviews·Ian FlemingDavid Walter
Feb 26, 2004·Journal of the American Chemical Society·Qibin Su, James S Panek
Oct 8, 2004·Organic Letters·J Brad Shotwell, William R Roush
Jan 18, 2005·Angewandte Chemie·Qibin Su, James S Panek

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Citations

Dec 3, 2010·The Journal of Organic Chemistry·Scott E DenmarkJoseck M Muhuhi
Dec 30, 2010·Organic Letters·Jihoon Lee, James S Panek
Oct 1, 2011·Chemistry : a European Journal·Bin ChengHongbin Zhai
Mar 1, 2012·Chemistry : a European Journal·Julián BergueiroSusana López
Sep 10, 2009·Organic Letters·Jihoon Lee, James S Panek
May 25, 2010·Organic Letters·Hannah F SoreDavid R Spring
Dec 15, 2010·The Journal of Organic Chemistry·Phil Ho LeeHyonseok Hwang
Mar 5, 2015·The Journal of Organic Chemistry·Jihoon Lee, James S Panek
Jan 16, 2007·Organic Letters·Jason T LoweJames S Panek

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