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首页> 外文期刊>Chemistry: A European journal >Complete stereocontrol in organocatalytic additions of β- ketosulfoxides to conjugated aldehydes
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Complete stereocontrol in organocatalytic additions of β- ketosulfoxides to conjugated aldehydes

机译：β-酮亚砜与共轭醛有机催化加成中的完全立体控制

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摘要

The use of β-ketosulfoxides as nucleophiles in reactions with α,β-unsaturated aldehydes catalyzed by proline derivatives allows complete control of configuration at the two chiral centers that are created during 1,4-addition reactions. The sulfinyl group can be used to create additional chiral centers in the resulting compounds and then removed while preserving the chirality of the carbon joined to the sulfur. The catalyst and the sulfinyl group are mainly responsible for the configurational control of the carbon atoms acting as electrophile and nucleophile, respectively, which allows the preparation of the four possible diastereoisomers in optically pure form. Theoretical calculations of the possible chiral nucleophilic species bearing diastereotopic faces allow us to postulate, for the first time, that enolates, instead of enols, are the active reagents in these reactions.
机译：在脯氨酸衍生物催化的α，β-不饱和醛反应中使用β-酮亚砜作为亲核试剂，可以完全控制在1,4-加成反应过程中产生的两个手性中心的构型。亚磺酰基可用于在所得化合物中产生另外的手性中心，然后在保留与硫连接的碳的手性的同时被除去。催化剂和亚磺酰基主要负责分别控制作为亲电子试剂和亲核试剂的碳原子的构型控制，这允许制备光学纯形式的四种可能的非对映异构体。对带有非对映体面的可能手性亲核物质的理论计算使我们首次假定烯醇而不是烯醇是这些反应中的活性试剂。

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