一类新型的取代芳基双（恶唑啉）配体，用于铜催化的二烯醇硅烷与丙酮酸酯和乙醛酸酯的高对映选择性不对称羟醛加成反应。

A new class of substituted aryl bis(oxazoline) ligands for highly enantioselective copper-catalyzed asymmetric aldol addition of dienolsilane to pyruvate and glyoxylate esters.

作者信息

Le Julie Cong-Dung, Pagenkopf Brian L

机构信息

The Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA.

出版信息

Org Lett. 2004 Oct 28;6(22):4097-9. doi: 10.1021/ol048179w.

DOI:10.1021/ol048179w

PMID:15496108

Abstract

[reaction: see text] A new class of bis(oxazoline) ligands are introduced that feature o-alkoxyaryl substituents and provide the highest enantioselectivities yet reported for the copper-catalyzed asymmetric dienosilane aldol addition to pyruvate and glyoxylate esters. Enantioselectivities up to 98% ee (before recrystallization) and isolated yields up to 91% were observed. Additionally, chloride counterions were found to be superior to triflate for this reaction.

摘要

[反应：见正文] 引入了一类新型的双（恶唑啉）配体，其具有邻烷氧基芳基取代基，并且对于铜催化的丙酮酸酯和乙醛酸酯的不对称二烯硅烷醇醛加成反应提供了迄今报道的最高对映选择性。观察到对映选择性高达98% ee（重结晶前），分离产率高达91%。此外，发现氯离子抗衡离子对于该反应优于三氟甲磺酸根离子。