CHROMIUM DIRECTED REGIOCONTROL AND STEREOCONTROL - A NEW CHAPTER IN AROMATIC NATURAL PRODUCT SYNTHESIS

被引：42

作者：

DICKENS, PJ

GILDAY, JP

NEGRI, JT

WIDDOWSON, DA

机构：

[1] Department of Chemistry, Imperial College, Londor

来源：

PURE AND APPLIED CHEMISTRY | 1990年 / 62卷 / 04期

关键词：

D O I：

10.1351/pac199062040575

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The sequence of ortho-directing abilities of a series of aryl functionalities in arenetricarbonylchromium(O) complexes has been shown to be different to that in the uncomplexed arenes. The kinetic resolution of the lithiated complexes with homochiral oxazolidinones has been rationalised via a transition state model and applied to the stereocontrolled synthesis of a series of highly functionalised, homochiral phenethylamines. © 1990, IUPAC.

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页码：575 / 581

页数：7

相关论文

共 28 条

[1] MECHANISTIC EVIDENCE FOR ORTHO-DIRECTED LITHIATIONS FROM ONE-DIMENSIONAL AND TWO-DIMENSIONAL NMR-SPECTROSCOPY AND MNDO CALCULATIONS [J].

BAUER, W ;

SCHLEYER, PV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (18) :7191-7198

[2] A COMPARISON OF SECONDARY AND TERTIARY AMIDES AS DIRECTORS OF ORTHO AND ADJACENT BENZYLIC LITHIATION AND OF ASYMMETRIC INDUCTION IN ORTHO LITHIATED BENZAMIDES [J].

BEAK, P ;

TSE, A ;

HAWKINS, J ;

CHEN, CW ;

MILLS, S .

TETRAHEDRON, 1983, 39 (12) :1983-1989

[3] ORTHO-LITHIOTHIOPHENOL EQUIVALENTS - GENERATION, REACTIONS, AND APPLICATIONS IN SYNTHESIS OF HINDERED THIOLATE LIGANDS [J].

BLOCK, E ;

ESWARAKRISHNAN, V ;

GERNON, M ;

OFORIOKAI, G ;

SAHA, C ;

TANG, K ;

ZUBIETA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) :658-665

[4] TRANSITION-METAL MEDIATED ORGANIC-SYNTHESIS - THE SYNTHESIS OF MORACIN-M [J].

CLOUGH, JM ;

MANN, IS ;

WIDDOWSON, DA .

TETRAHEDRON LETTERS, 1987, 28 (23) :2645-2648

[5] STRUCTURAL STUDIES OF BENZENE-DERIVATIVES .5. CRYSTAL AND MOLECULAR-STRUCTURE OF P-FLUOROBENZOIC ACID [J].

COLAPIETRO, M ;

DOMENICANO, A ;

CECCARINI, GP .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1979, 35 (APR) :890-894

[6] COMPLEMENTARY STEREOSELECTIVE CYCLIZATIONS OF N-(3,4-DIMETHOXYBENZYL)EPHEDRINE AND ITS CHROMIUM TRICARBONYL COMPLEX TO TRANS AND CIS-2,3-DIMETHYL-4-PHENYL-6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINES RESPECTIVELY [J].

COOTE, SJ ;

DAVIES, SG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (10) :648-649

[7] ASYMMETRIC-SYNTHESIS OF ALPHA-SUBSTITUTED ORTHO-METHOXYBENZYL ALCOHOLS VIA STEREOSELECTIVE ADDITIONS TO KINETICALLY RESOLVED ORTHO-ANISALDEHYDE-(TRICARBONYL)CHROMIUM [J].

DAVIES, SG ;

GOODFELLOW, CL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (01) :192-194

[8]

Davies SG, 1989, SYNLETT, P59

[9]

DICKENS MJ, 1989, THESIS LONDON U

[10]

DOMENICANO A, 1979, ACTA CRYSTALLOGR B, V35, P1392