New Adaptive Chiral Thiophene Ligands for Copper-Catalyzed Asymmetric Henry Reaction

被引：18

作者：

Bandini, Marco ^{[1
]}

Cabiddu, Salvatore ^{[2
]}

Cadoni, Enzo ^{[2
]}

Olivelli, Pasquale ^{[1
]}

Sinisi, Riccardo ^{[1
]}

Umani-Ronchi, Achille ^{[1
]}

Usai, Michele ^{[2
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, Alma Mater Studiorum, I-40126 Bologna, Italy

[2] Univ Cagliari, Dipartimento Sci Chim, Cagliari, Italy

来源：

CHIRALITY | 2009年 / 21卷 / 01期

关键词：

asymmetric catalysis; chiral diamine ligands; copper; nitroaldol reaction; thiophene; DIAMINO-OLIGOTHIOPHENES; COMPLEXES;

D O I：

10.1002/chir.20613

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new type of adaptive chiral thiophene-based ligands 3 has been designed and developed. The synthetic flexibility of the thienyl ring allowed for the preparation of polydendate C2-symmetric ligands in good yields, carrying simultaneously "hard" as well as "soft" coordinating atoms (i.e., N, S). The coordination attitude of 3 was then tested in the enantioselective base-free Cu(OAc)(2)-catalyzed addition of nitromethane to aromatic aldehydes, leading to the corresponding P-nitro alcohols in excellent yields and enantiomeric excesses up to 86%. Chirality 21:239-244, 2009. (c) 2008 Wiley-Liss, Inc.

引用

页码：239 / 244

页数：6

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