Direct carbon-carbon bond formation via reductive soft enolization: a kinetically controlled syn-aldol addition of α-halo thioesters and enolizable aldehydes.
نویسندگان
چکیده
The direct addition of enolizable aldehydes and α-halo thioesters to produce β-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 α-hydroxy aldehyde derivative is used.
منابع مشابه
Direct carbon-carbon bond formation via soft enolization: aldol addition of α-halogenated thioesters.
α-Halo thioesters undergo soft enolization and syn-selective direct aldol addition to aldehydes in the presence of MgBr(2)·OEt(2) and i-Pr(2)NEt to produce α-halo-β-hydroxy thioesters.
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عنوان ژورنال:
- Journal of the American Chemical Society
دوره 132 40 شماره
صفحات -
تاریخ انتشار 2010