New chiral diphosphoramidite rhodium(I) complexes for asymmetric hydrogenation

被引：8

作者：

Drommi, Dario ^{[1
]}

Micalizzi, Giuseppe ^{[1
]}

Arena, Carmela Grazia ^{[1
]}

机构：

[1] Univ Messina, Dipartimento Sci Chim, I-98166 Messina, Italy

来源：

APPLIED ORGANOMETALLIC CHEMISTRY | 2014年 / 28卷 / 08期

关键词：

diphosphoramidite; asymmetric hydrogenation; rhodium; hydrogen pressure; ENANTIOSELECTIVE HYDROGENATION; PHOSPHITE LIGANDS; RECENT TRENDS; ACID; (R,R)-1,2-DIAMINOCYCLOHEXANE; PHOSPHORAMIDITES; CATALYSIS; OLEFINS; P-31;

D O I：

10.1002/aoc.3170

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Chiral 1,5-cyclooctadiene rhodium(I) cationic complexes with C-2-symmetric chelate diphosphoramidite ligands containing (R,R)-1,2-diaminocyclohexane as the backbone and two atropoisomeric biaryl units were easily synthesized and fully characterized by multinuclear one- and two-dimensional NMR spectroscopy and elemental analysis. These complexes were used as catalysts in the asymmetric hydrogenation of dimethyl itaconate, methyl 2-acetamidoacrylate and (Z)-methyl-2-acetamido-3-phenylacrylate. The rhodium complexes derived from diphosphoramidite ligands that contain two (R) or (S) BINOL (2,2'-dihydroxy-1,1'-binaphthyl) units proved to be efficient catalysts, giving complete conversion and very good enantioselectivity (up to 88% ee). An uncommon positive H-2 pressure effect on the enantioselectivity was observed in the hydrogenation of dimethyl itaconate catalyzed by Rh-complex with diphosphoramidite ligand that contains two (S)-binaphthol moieties. Copyright (C) 2014 John Wiley & Sons, Ltd.

引用

页码：614 / 619

页数：6

共 47 条

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