Stereoselectivity of the Ortho Ester Claisen Rearrangement of Substituted Silylpropargylic Alcohols

摘要: The ortho ester Claisen rearrangement has been very useful synthetic methodology in organic synthesis. of the propargylic alcohols effective method for producing corresponding allene esters biologically significant. Particularly involving a β-substituted vinyl participant is potentially powerful reaction because diastereomeric product may be generated. However, only one example yielding 1,3-disubstituted allenes by examined using substituted secondary propynyl Heathcocks group. His group was able to obtain high stereoselectivity (80-90% syn selectivity) alcohol bearing bulky alkyl at C-1 position. results are noteworthy due fact that diastereoselectivity generally moderate or poor mixture E and Z moiety intermediate ketene acetal 2c,4 silylpropargylic might an efficient route stereo-defined silylallenes which intermediates Therefore, study on 1-alkyl-3-silylpropynol 2 leading 3 reported this paper.