A kinetically controlled direct aldol addition of α-chloro thioesters via soft enolization
2017
Alfie, Rachel J. | Trương, Ngọc | Yost, Julianne M. | Coltart, Don M.
Herein we report that simple α-chloro thioesters undergo soft enolization and direct aldol addition to aldehydes in the presence of MgBr2·OEt2 and i-Pr2NEt. At −78°C the reaction proceeds in a kinetically controlled manner giving good diastereoselectivity. Significantly, the transformation is applicable to both enolizable and nonenolizable aldehydes. Moreover, excellent stereoselectivity results when a chiral nonracemic α-hydroxy aldehyde derivative is used. To our knowledge, this is the first report of a kinetically controlled soft enolization-based aldol addition.
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