通过烯醇盐的钯催化不对称烯丙基烷基化对α-叔羟基醛进行对映选择性合成。
Enantioselective synthesis of alpha-tertiary hydroxyaldehydes by palladium-catalyzed asymmetric allylic alkylation of enolates.
作者信息
Trost Barry M, Xu Jiayi, Reichle Markus
机构信息
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
出版信息
J Am Chem Soc. 2007 Jan 17;129(2):282-3. doi: 10.1021/ja067342a.
Abstract
Chiral α-tertiary hydroxyaldehydes are very versatile building blocks in synthetic chemistry. Herein, we reported the first examples of a catalytic asymmetric protocol for the synthesis of such compounds from readily available α-halo or α-hydroxy ketones or enol silyl ethers with excellent yields and enantioselectivity. Its synthetic utility is demonstrated in the short, efficient formal synthesis of ()-oxybutynin. In this process, the chiral ligand controls with the regioselectivity as well as enantioselectivity.
摘要
手性α-叔羟基醛是合成化学中非常通用的结构单元。在此，我们报道了首例从易得的α-卤代或α-羟基酮或烯醇硅醚出发，以优异的产率和对映选择性合成此类化合物的催化不对称方法。其合成实用性在()-奥昔布宁的简短、高效形式合成中得到了证明。在这个过程中，手性配体控制区域选择性和对映选择性。
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