Synthesis of the novel chiral 1,3-amino alcohol 8-N,N-bis(ferrocenylmethyl)amino-menthol and its use as catalyst in the enantioselective addition of diethylzinc to aldehydes

被引：42

作者：

Vilaplana, MJ

Molina, P

Arques, A

Andrés, C

Pedrosa, R

机构：

[1] Univ Murcia, Fac Quim, Dept Quim Organ, E-30100 Murcia, Spain

[2] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47011 Valladolid, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 01期

关键词：

D O I：

10.1016/S0957-4166(02)00063-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Optically active 8-N,N-bis(ferrocenylmetllyl)aminomenthol 5. obtained by condensation of (-)-aminomenthol with ferrocenecarboxaldehyde followed by N-alkylation with (ferrocenylmethyl)trimethylammonium iodide and further reduction, was found to catalyze (5 mol%) the enantioselective ethylation of aromatic. aliphatic and organometallic aldehydes to secondary alcohols with high enantioselectivities (up to 95%) at room temperature. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5 / 8

页数：4

共 10 条

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[3] ORGN 982-The synthesis of novel chiral 1,2-amino alcohols and their use in directing the addition of diethylzinc to aromatic aldehydes
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[4] Synthesis of N,N-dimethyl-2-amino-1,2-dicyclohexylethanol and its application in the enantioselective conjugate addition of diethylzinc to enones:: a convenient upgrade of the chiral ligand via hydrogenation
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Qian Yong XU1
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[6] HEXAHYDROPYRIMIDINES .8. SYNTHESIS OF 2-SUBSTITUTED 1,3-BIS[4-[N,N-BIS(2-CHLOROETHYL)AMINO]BENZYL] HEXAHYDROPYRIMIDINES AS TRANSPORT MOLECULES FOR TUMOR INHIBITION
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[7] Catalytic enantioselective reactions .9. 1,2-O-isopropylidene-5-deoxy-5-N,N-dialkyl (or -N-monoalkyl)amino-alpha-D-xylofuranose derivatives as highly-effective chiral catalysts for enantioselective addition of diethylzinc to aliphatic and aromatic aldehydes
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[8] Lewis acid mediated SN2-type nucleophilic ring opening followed by [4+2] cycloaddition of N-tosylazetidines with aldehydes and ketones:: synthesis of chiral 1,3-oxazinanes and 1,3-amino alcohols
Ghorai, Manas K.
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[9] Synthesis of N-alkylated and N-arylated derivatives of 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN) and 2,2′-diamino-1,1′-binaphthyl and their application in the enantioselective addition of diethylzinc to aromatic aldehydes
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[10] Synthesis of Enantiopure Trans-N-Boc-3-Aminobicyclo[2.2.2]octane-2-carboxylic acids and Their Bicyclic 1,3-Amino alcohol Derivatives via the [4+2] Cycloaddition of 1,3-Cyclohexadiene to a Chiral β-Nitroacrylate
Calmes, Monique
Escale, Francoise
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