REGIO- AND STEREOSELECTIVE ALCOHOLYSIS OF (R)-STYRENE OXIDE WITH BIS-TRIBUTYLTIN OXIDE AND BIS-CHLORODIBUTIYLTIN OXIDE
Salomon, Claudio J., Laborde, Maria A., Sierra, Manuel G. and 1 more
Main Group Metal Chemistry · 1998
doi:10.1515/mgmc.1998.21.10.617 (opens in a new tab)
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Abstract
We report herein a convenient method for the regio-and stereoselective ringopening of (R)-styrene oxide (1) by means of primary and secondary alcohols, using bis-tributyltin oxide (2) and bis-chlorodibutyltin oxide (3) as Lewis acids, in catalytic or in stoichiometric amount.The alcoholysis of (fl)-styrene oxide has been found to proceed with very good regio-and stereoselectivity affording the corresponding 2-alcoxy-2-phenylethanol.Alcohols attacks at the benzylic position almost exclusively.
Abstract licence: CC BY-NC-ND
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