Cu(II)-Macrocylic [H4]Salen Catalyzed Asymmetric Nitroaldol Reaction and Its Application in the Synthesis of α1-Adrenergic Receptor Agonist (R)-Phenylephrine

被引：75

作者：

Kureshy, Rukhsana I. ^{[1
]}

Das, Anjan ^{[1
]}

Khan, Noor-ul H. ^{[1
]}

Abdi, Sayed H. R. ^{[1
]}

Bajaj, Hari C. ^{[1
]}

机构：

[1] Cent Salt & Marine Chem Res Inst CSIR CSMCRI, Discipline Inorgan Mat & Catalysis, Bhavnagar 364021, Gujarat, India

来源：

ACS CATALYSIS | 2011年 / 1卷 / 11期

关键词：

enantioselective; chiral Cu(II) macrocyclic complexes; chiral beta-nitroalcohols; aldehydes; recyclable; ENANTIOSELECTIVE HENRY REACTION; SALEN-CHROMIUM COMPLEXES; CHIRAL COPPER-COMPLEXES; AMINO-ALCOHOLS; BASE CATALYSIS; LIGANDS; BIS(THIAZOLINE); BIS(OXAZOLINE); DERIVATIVES; ACTIVATION;

D O I：

10.1021/cs2004467

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

New chiral Cu (II) complexes 1-6 were generated in situ by the interaction of different sources of copper(II) salts with chiral monomeric and dimeric macrocyclic [H-4]salen ligands derived from (1R,2R)-(-)-1,2-diaminocyclohexane and (1R,2R)-(-)-1,2-diphenyl-1,2-diaminoethane with trigol-bis(aldehyde). A variety of aldehydes were found to be suitable substrates with nitromethane in the presence of chiral macrocyclic [H-4]salen complexes 1-6 for asymmetric nitroaldol reaction at RT. Excellent yields (98% with respect to the aldehyde) of beta-nitroalcohols with high enantioselectivity (ee, similar to 99%) were achieved in the case of 2-fluorobenzaldehyde in similar to 20 h with the use of chiral mononuclear and dinuclear macrocyclic Cu(II) salen complexes 2 and 5. Both chiral mononuclear and dinuclear macrocyclic [H-4]salen catalysts 2- and 5-mediated nitroaldol processes are recyclable (up to eight cycles with no significant loss in its performance).

引用

页码：1529 / 1535

页数：7

共 68 条

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