Highly stereoselective alkylation through asymmetric intramolecular autoactivation; Synthesis and use of a new chiral ligand

被引：20

作者：

Maciejewski, LA ^{[1
]}

Goetgheluck, SJ ^{[1
]}

Delacroix, OA ^{[1
]}

Brocard, JS ^{[1
]}

机构：

[1] UNIV SCI & TECHNOL,URA CNRS 402,GRP SYNTH ORGANOMET,CATALYSE HETEROGENE & HOMOGENE LAB,F-59655 VILLENEUVE DASCQ,FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 06期

关键词：

D O I：

10.1016/0957-4166(96)00184-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The ethylation of 2-(N,N-dimethylaminomethyl)ferrocenylcarboxaldehyde 1 without a catalyst is stereospecific and occurs with high rates, yields and diastereoselectivities through an intramolecular asymmetric autoactivation. This reaction allowed the synthesis of the enantiopure (+)-(S,1S)-(2-(N,N-dimethyl-aminomethyl)ferrocenyl)-1-propanol 2 by applying this result to the enantiomerically pure aldehyde 1. This new chiral auxiliary acted as a catalyst during the ethylation of benzaldehyde with diethylzinc. (C) 1996 Published by Elsevier Science Ltd

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页码：1573 / 1576

页数：4

相关论文

共 36 条

[1] THE ROLE OF THE PRODUCT IN ASYMMETRIC C-C BOND FORMATION - STOICHIOMETRIC AND CATALYTIC ENANTIOSELECTIVE AUTOINDUCTION [J].

ALBERTS, AH ;

WYNBERG, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (18) :7265-7266

[2]

BATELLE LF, 1973, J AM CHEM SOC, V95, P482

[3] CATALYTIC ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES - SYNTHESIS AND APPLICATION OF A NEW CYCLIC CATALYST [J].

BEHNEN, W ;

MEHLER, T ;

MARTENS, J .

TETRAHEDRON-ASYMMETRY, 1993, 4 (07) :1413-1416

[4] SUCCESSIVE REGIOSPECIFIC AND STEREOSPECIFIC FUNCTIONALIZATION OF ETA(6)-ARENETRICARBONYLCHROMIUM IN POSITIONS META AND ORTHO [J].

BROCARD, J ;

GOETGHELUCK, S ;

PELINSKI, L .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 476 (01) :C12-C14

[5] ENANTIOSELECTIVE ADDITION OF N-BUTYLLITHIUM TO BENZALDEHYDE IN THE PRESENCE OF CHIRAL LITHIUM AMIDES [J].

ELEVELD, MB ;

HOGEVEEN, H .

TETRAHEDRON LETTERS, 1984, 25 (45) :5187-5190

[6] CHIRAL TITANIUM ALKOXIDES AS CATALYSTS FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES WITH BORANES [J].

GIFFELS, G ;

DREISBACH, C ;

KRAGL, U ;

WEIGERDING, M ;

WALDMANN, H ;

WANDREY, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (18) :2005-2006

[7]

GLORIAN G, IN PRESS

[8]

GOETGHELUCK S, IN PRESS J ORGANOMET

[9] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-TRANSITION METAL-COMPLEXES .10. GOLD(I)-CATALYZED ASYMMETRIC ALDOL REACTION OF ISOCYANOACETATE [J].

HAYASHI, T ;

SAWAMURA, M ;

ITO, Y .

TETRAHEDRON, 1992, 48 (11) :1999-2012

[10] OPTICALLY-ACTIVE N-1-PHENYLETHYL DERIVATIVES OF (1R)-2-AMINO-1-PHENYLETHANOL AS CHIRAL AUXILIARIES IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ARYLALDEHYDES [J].

IULIANO, A ;

PINI, D ;

SALVADORI, P .

TETRAHEDRON-ASYMMETRY, 1995, 6 (03) :739-744

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