Catalytic enantioselective synthesis of the second generation histamine antagonist cetirizine hydrochloride

被引：104

作者：

Corey, EJ

Helal, CJ

机构：

[1] Department of Chemistry, Harvard University, Cambridge

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 28期

关键词：

D O I：

10.1016/0040-4039(96)00964-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first enantioselective synthesis of cetirizine hydrochloride (I) has been developed using the highly stereospecific chiral oxazaborolidine (CBS) reduction of 4-[eta(6)-chromium tricarbonylbenzoyl]chlorobenzene to establish the benzhydryl stereocenter. The chromium tricarbonyl unit also served as stereocontroller to allow the stereospecific displacement of hydroxyl by amino at the benzylic stereocenter, as outlined in Scheme I. Copyright (C) 1996 Elsevier Science Ltd

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页码：4837 / 4840

页数：4

相关论文

共 10 条

[1] SYNTHETIC APPLICATIONS OF LITHIATED TRICARBONYL-ETA-6-ARENECHROMIUM(O) COMPLEXES - COPPER AND PALLADIUM CATALYZED SUBSTITUTIONS [J].

BESWICK, PJ ;

LEACH, SJ ;

MASTERS, NF ;

WIDDOWSON, DA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (01) :46-48

[2]

BUDAVARI S, 1989, MERCK INDEX, P310

[3] RECOVERY OF CR(CO)3 UNIT IN REMOVAL OF ORGANIC-LIGANDS FROM THEIR CHROMIUM CARBONYL-COMPLEXES [J].

CARGANICO, G ;

DELBUTTERO, P ;

MAIORANA, S ;

RICCARDI, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (22) :989-990

[4] NOVEL ELECTRONIC EFFECTS OF REMOTE SUBSTITUENTS ON THE OXAZABOROLIDINE-CATALYZED ENANTIOSELECTIVE REDUCTION OF KETONES [J].

COREY, EJ ;

HELAL, CJ .

TETRAHEDRON LETTERS, 1995, 36 (50) :9153-9156

[5]

JAOUEN C, 1978, TRANSITION METAL ORG, V2, pCH2

[6]

OPALKA CJ, 1995, SYNTHESIS-STUTTGART, P766

[7] METALATION OF ARENECHROMIUM TRICARBONYL COMPLEXES AND ELECTROPHILIC TRAPPING OF THE COMPLEXED PHENYLLITHIUM INTERMEDIATE [J].

SEMMELHACK, MF ;

BISAHA, J ;

CZARNY, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (03) :768-770

[8] CETIRIZINE - A REAPPRAISAL OF ITS PHARMACOLOGICAL PROPERTIES AND THERAPEUTIC USE IN SELECTED ALLERGIC DISORDERS [J].

SPENCER, CM ;

FAULDS, D ;

PETERS, DH .

DRUGS, 1993, 46 (06) :1055-1080

[9] N-ALKYLATION OF NITRILES USING CHROMIUM TRICARBONYL COMPLEXES OF BENZYL ALCOHOL AND ITS DERIVATIVES - NEW PERSPECTIVES FOR THE RITTER REACTION [J].

TOP, S ;

JAOUEN, G .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (01) :78-82

[10] DIASTEREOSELECTIVE ADDITION OF 2-BUTENYLMETAL ATE COMPLEXES TO AROMATIC KETONES MEDIATED BY CR(CO)3 COMPLEXATION [J].

UEMURA, M ;

MINAMI, T ;

ISOBE, K ;

KOBAYASHI, T ;

HAYASHI, Y .

TETRAHEDRON LETTERS, 1986, 27 (08) :967-970