Direct Carbon-Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of α-Halo Thioesters and Enolizable Aldehydes
Direct Carbon-Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of α-Halo Thioesters and Enolizable Aldehydes
复制标题
DOI：
10.1021/ja1057407
复制
发表时间：
2010-10-13
影响因子：
15
通讯作者：
Coltart, Don M.
中科院分区：
文献类型：
--
作者：
Sauer, Scott J.;Garnsey, Michelle R.;Coltart, Don M.
报道了可烯醇化的醛和α-卤代硫酯的直接加成，以通过还原性软烯醇化来产生β-羟基硫酯。该转化操作简单且有效，并且具有提供高顺式选择性的不寻常特征，这与在常规条件下产生的（硫代）酯相反。此外，当使用手性非外消旋α-羟基醛衍生物时，产生优异的非对映选择性。
The direct addition of enolizable aldehydes and alpha-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.