TRANSITION-METAL MEDIATED ASYMMETRIC-SYNTHESIS .15. DIRECTING GROUP COMPETITION IN ORGANOIRON INTERMEDIATES IN THE SYNTHESIS OF (+/-)-O-METHYLJOUBERTIAMINE

被引：42

作者：

STEPHENSON, GR ^{[1
]}

FINCH, H ^{[1
]}

OWEN, DA ^{[1
]}

SWANSON, S ^{[1
]}

机构：

[1] GLAXO GRP RES LTD,WARE SG12 0DJ,HERTS,ENGLAND

来源：

TETRAHEDRON | 1993年 / 49卷 / 25期

关键词：

D O I：

10.1016/S0040-4020(01)87274-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Directing groups work first in concert and then in competition to control the introduction of aryl and 2-dimethylaminoethyl groups by a sequence of two nucleophile additions to cationic tricarbonyl(eta5-cyclohexadienyl)iron(1+) intermediates in a synthesis of O-methyljoubertiamine that employs an iterative approach. This synthesis provides an example of the successful use of directing group competition to effect the reversal of undesired directing effects in target oriented applications of electrophilic pi-complexes.

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页码：5649 / 5662

页数：14

相关论文

共 81 条

[11] ORGANOMETALLIC COMPOUNDS IN ORGANIC-SYNTHESIS .11. THE STRATEGY OF LATERAL CONTROL OF REACTIVITY - TRICARBONYLCYCLOHEXADIENEIRON COMPLEXES AND THEIR ORGANIC SYNTHETIC EQUIVALENTS [J].

BIRCH, AJ ;

BANDARA, BMR ;

CHAMBERLAIN, K ;

CHAUNCY, B ;

DAHLER, P ;

DAY, AI ;

JENKINS, ID ;

KELLY, LF ;

KHOR, TC ;

KRETSCHMER, G ;

LIEPA, AJ ;

NARULA, AS ;

RAVERTY, WD ;

RIZZARDO, E ;

SELL, C ;

STEPHENSON, GR ;

THOMPSON, DJ ;

WILLIAMSON, DH .

TETRAHEDRON, 1981, 37 :289-302

[12] RATES OF REACTION OF PENTANE-2,4-DIONE WITH SOME SUBSTITUTED TRICARBONYLCYCLOHEXADIENYL IRON CATIONS [J].

BIRCH, AJ ;

BOGSANYI, D ;

KELLY, LF .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 214 (03) :C39-C42

[13] CHEMISTRY OF CO-ORDINATED LIGANDS .2. IRON TRICARBONYL COMPLEXES OF SOME CYCLOHEXADIENES [J].

BIRCH, AJ ;

CROSS, PE ;

LEWIS, J ;

WHITE, DA ;

WILD, SB .

JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1968, (02) :332-&

[14] REGIOSELECTIVITY OF NUCLEOPHILIC ADDITIONS TO TRICARBONYL[ETA-5-2-METHYL-2,4-CYCLOHEXADIEN-1-YL]IRON(1+)PF6(-) - TEMPERATURE-DEPENDENCE OF HYDRIDE REDUCTIONS [J].

BIRCH, AJ ;

STEPHENSON, GR .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 218 (01) :91-104

[15] ORGANO-METALLIC COMPOUNDS IN ORGANIC-SYNTHESIS .17. REACTIONS OF TRICARBONYLCYCLOHEXADIENYLIRON SALTS WITH O-SILYLATED ENOLATES, ALLYL SILANES AND ASPECTS OF THEIR SYNTHETIC EQUIVALENTS [J].

BIRCH, AJ ;

KELLY, LF ;

NARULA, AS .

TETRAHEDRON, 1982, 38 (12) :1813-1823

[16] CHIRALITY TRANSFER IN THE COORDINATION SPHERE OF IRON [J].

BIRCH, AJ ;

RAVERTY, WD ;

STEPHENSON, GR .

ORGANOMETALLICS, 1984, 3 (07) :1075-1079

[17] A FACILE SYNTHESIS OF (+)-SHIKIMIC AND (-)-SHIKIMIC ACID WITH ASYMMETRIC DEUTERIUM LABELING, USING TRICARBONYLIRON AS A LATERAL CONTROL-GROUP [J].

BIRCH, AJ ;

KELLY, LF ;

WEERASURIA, DV .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (02) :278-281

[18] TRICARBONYLIRON METHOXYCYCLOHEXADIENE AND DIENYL COMPLEXES - PREPARATION, PROPERTIES AND APPLICATIONS [J].

BIRCH, AJ ;

KELLY, LF .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 285 (1-3) :267-280

[19] ORGANOMETALLIC COMPOUNDS IN ORGANIC-SYNTHESIS .10. PREPARATIONS AND SOME REACTIONS OF TRICARBONYL-1,3 AND 1,4-DIMETHOXYCYCLOHEXA-1,3-DIENEIRON AND RELATED-COMPOUNDS - THE PREPARATION OF THE TRICARBONYL-3-METHOXYCYCLOHEXADIENYLIUMIRON CATION [J].

BIRCH, AJ ;

KELLY, LF ;

THOMPSON, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (04) :1006-1012

[20]

BIRCH AJ, 1982, TETRAHEDRON LETT, V1, P2981

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