New proline-oxazoline ligands and their application in the asymmetric Nozaki-Hiyama-Kishi reaction

被引：46

作者：

Hargaden, Grainne C. ^{[1
]}

Mueller-Bunz, Helge ^{[1
]}

Guiry, Patrick J. ^{[1
]}

机构：

[1] Univ Coll Dublin, Sch Chem & Chem Biol, Conway Inst Biomol & Biomed Res, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 25期

关键词：

asymmetric catalysis; oxazolines proline; ligands; allylation;

D O I：

10.1002/ejoc.200700227

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sixteen members of a new ligand class incorporating an oxazoline ring linked by an amide bond to a chiral protected proline unit were prepared in a high-yielding four-step synthesis from readily available chiral amino alcohols and N-protected proline. The ligands were applied in the enantio-selective Nozaki-Hiyama-Kishi allylation of benzaldehyde and gave enantioselectivities of up to 57%. Diastereomeric ligand pairs were prepared to determine the role of each chiral centre in enantioselection. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).

引用

页码：4235 / 4243

页数：9

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