Browsing by Subject "triethylamine"
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Item Restricted Direct Carbon-Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of alpha-Halo Thioesters and Enolizable Aldehydes(2010) Sauer, Scott J; Garnsey, Michelle R; Coltart, Don MThe direct addition of enolizable aldehydes and a-halo thioesters to produce beta-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-selectivity, which is the opposite of that produced for (thio)esters under conventional conditions. Moreover, excellent diastereoselectivity results when a chiral nonracemic alpha-hydroxy aldehyde derivative is used.Item Open Access Direct carbon-carbon bond formation via soft enolization: aldol addition of alpha-halogenated thioesters(2011) Yost, Julianne M; Alfie, Rachel J; Tarsis, Emily M; Chong, Insun; Coltart, Don Malpha-Halo thioesters undergo soft enolization and syn-selective direct aldol addition to aldehydes in the presence of MgBr2 center dot OEt2 and i-Pr2NEt to produce alpha-halo-beta-hydroxy thioesters.