Design of a small-molecule catalyst using intramolecular cation-π interactions for enantioselective Diels-Alder and Mukaiyama-Michael reactions:: L-DOPA-derived monopeptide-Cu(II) complex

被引：72

作者：

Ishihara, K ^{[1
]}

Fushimi, M ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Nagoya, Aichi 4648603, Japan

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 09期

关键词：

D O I：

10.1021/ol060651l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have designed a small-molecule artificial metalloenzyme that is prepared in situ from Cu(OTf)(2) or Cu(NTf2)(2) (1.0 equiv) and L-DOPA-derived monopepticle (1.1 equiv). This catalyst (2-10 mol %) is highly effective for the enantioselective Diels-Alder (DA) and Mukaiyama-Michael (MM) reactions with (alpha,beta unsaturated 1-acyl-3,5-dimethylpyrazoles. The present results demonstrate that cation-pi interactions may be available for controlling the conformation of sidearms of chiral ligands, and monopeptides are readily tunable ligands that include only one chiral center.

引用

页码：1921 / 1924

页数：4

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