Enantiomerically pure phosphaferrocenes with planar chirality

被引：49

作者：

Ganter, C

Brassat, L

Ganter, B

机构：

[1] Inst. für Anorganische Chemie, Technische Hochschule Aachen

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 15期

关键词：

D O I：

10.1016/S0957-4166(97)00273-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiomerically pure 2-formyl-3,4-dimethylphosphaferrocene 1 was prepared straightforwardly by resolution of rac-1 via column chromatography on silica of diastereomeric aminals formed of 1 and (R),(R)-1,2-di(N-methylamino)cyclohexane 2. Both enantiomers (S)-1 and (R)-1 are obtained in 94% yield with ee>99%. The amine 2 is recycled in 89% yield. The absolute configuration of (S)-1 has been determined by X-ray crystallography. (C) 1997 Elsevier Science Ltd.

引用

页码：2607 / 2611

页数：5

共 23 条

[1] Chiral aminals: Powerful auxiliaries in asymmetric synthesis
Alexakis, A
Mangeney, P
Lensen, N
Tranchier, JP
Gosmini, R
Raussou, S
[J]. PURE AND APPLIED CHEMISTRY, 1996, 68 (03) : 531 - 534
[2] A NEW REAGENT FOR THE DETERMINATION OF THE OPTICAL PURITY OF PRIMARY, SECONDARY, AND TERTIARY CHIRAL ALCOHOLS AND OF THIOLS
ALEXAKIS, A
MUTTI, S
MANGENEY, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) : 1224 - 1237
[3] RESOLUTION AND ASYMMETRIC-SYNTHESIS OF ORTHO-SUBSTITUTED (BENZALDEHYDE)TRICARBONYLCHROMIUM COMPLEXES
ALEXAKIS, A
MANGENEY, P
MAREK, I
ROSEMUNCH, F
ROSE, E
SEMRA, A
ROBERT, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) : 8288 - 8290
[4] [Anonymous], ADV METAL ORGANIC CH
[5] BAUER K, 1969, ANGEW CHEM, V81, P150
[6] STEREOSELECTIVE SYNTHESIS OF HOMOCHIRAL ALPHA SUBSTITUTED ORTHO-METHOXYBENZYL ALCOHOLS VIA NUCLEOPHILIC ADDITIONS TO KINETICALLY RESOLVED HOMOCHIRAL TRICARBONYL (ETA-6-ORTHO-ANISALDEHYDE)CHROMIUM(0)
BROMLEY, LA
DAVIES, SG
GOODFELLOW, CL
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (02) : 139 - 156
[7] TRICARBONYLPYRIDINECHROMIUM COMPLEXES - STEREOSELECTIVE ALKYLATIONS AND ALDOL-TYPE REACTIONS INVOLVING ALPHA-CARBANIONS DERIVED FROM ETA-TRICARBONYL(2-ALKYL-PYRIDINE)CHROMIUM COMPLEXES
DAVIES, SG
EDWARDS, AJ
SHIPTON, MR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (05): : 1009 - 1017
[8] 1,1'-DIPHOSPHAFERROCENES - SYNTHESIS, BASIC CHEMISTRY, AND STRUCTURE
DELAUZON, G
DESCHAMPS, B
FISCHER, J
MATHEY, F
MITSCHLER, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (03) : 994 - 1000
[9] Planar-chiral heterocycles as ligands in metal-catalyzed processes: Enantioselective addition of organozinc reagents to aldehydes
Dosa, PI
Ruble, JC
Fu, GC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (03) : 444 - 445
[10] ON ENANTIOMORPH-POLARITY ESTIMATION
FLACK, HD
[J]. ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV): : 876 - 881

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