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首页> 外文期刊>Chemistry: A European journal >S,O-acetals as novel 'chiral aldehyde' equivalents
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S,O-acetals as novel 'chiral aldehyde' equivalents

机译：S，O-缩醛作为新型“手性醛”的等同物

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摘要

Palladium-catalyzed asymmetric allylic alkylations (AAA) to form "chiral aldehyde" equivalents were investigated. alpha-Acetoxysulfones were formed in high enantiomeric excess as single regioisomers in AAA reactions of allylic geminal dicarboxylates with sodium benzenesulfinate. The directing ability of this novel functional group was highlighted by a series of dihydroxylations, affording syn diols exclusively anti to the acetoxy sulfone as single diastereomers in excellent yields. This is the first example of an asymmetric dihydroxylation protocol that gives the equivalent of reaction with a simple enal. The synthetic value of this process was exemplified by subsequent transformations of the diols including the development of a one-pot dihydroxylation-deprotective acyl migration protocol to give differentially protected 1,2-diols.
机译：研究了钯催化的不对称烯丙基烷基化（AAA）形成“手性醛”的等同物。 α-乙酰氧基砜在烯丙基双键双羧酸酯与苯亚磺酸钠的AAA反应中作为单一区域异构体以高对映体形式形成。一系列的二羟基化反应突出了这种新型官能团的定向能力，从而以优异的产率提供了对乙酰氧基砜具有独特抗性的单一非对映异构体。这是不对称二羟基化方案的第一个例子，它给出了与简单的烯醛相同的反应。该方法的合成价值以二醇的后续转化为例，包括开发一锅二羟基化-去保护性酰基迁移方案以得到差异保护的1,2-二醇。

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