Coupling of chiral 1-bromo-1,2-dienes with zinc-based cuprates: a new procedure for the regio and stereoselective synthesis of functionalized acetylenic compounds

被引：22

作者：

Caporusso, AM ^{[1
]}

Filippi, S ^{[1
]}

Barontini, F ^{[1
]}

Salvadori, P ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Chim & Chim, CNR, Ctr Studio Macromol Stereordinate & Otticamente A, I-56126 Pisa, Italy

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 08期

关键词：

coupling reactions; copper; copper compounds; allenes; alkynes;

D O I：

10.1016/S0040-4039(99)02249-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Zinc alkylcyanocuprates (Knochel reagents) are found to be active in the cross-coupling reaction with allenic bromides affording acetylenic products with a high regio and stereoselective 1,3-anti substitution. The coupling process, which has been successfully extended to functionalized cuprates, can also be performed with alkylzinc chlorides in the presence of catalytic amounts of cuprous salts. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：1227 / 1230

页数：4

相关论文

共 9 条

[1] METAL CATALYSIS IN ORGANIC-REACTIONS .18. STEREOCHEMISTRY OF THE TRANSITION-METAL CATALYZED CROSS-COUPLING OF "(S)-1-BROMO-3-METHYL-1,2-PENTADIENE WITH ISOBUTYLMETAL COMPOUNDS [J].

CAPORUSSO, AM ;

LARDICCI, L ;

DASETTIMO, F .

TETRAHEDRON LETTERS, 1986, 27 (09) :1067-1068

[2] REACTIONS OF 3-ALKYL-1-BROMOALLENES AND 3,3-DIALKYL-1-BROMOALLENES WITH ORGANOCUPRATES - EFFECTS OF THE NATURE OF THE CUPRATE REAGENT ON THE REGIOSELECTIVITY AND STEREOSELECTIVITY [J].

CAPORUSSO, AM ;

POLIZZI, C ;

LARDICCI, L .

TETRAHEDRON LETTERS, 1987, 28 (48) :6073-6076

[3]

CAPORUSSO AM, 1988, GAZZ CHIM ITAL, V118, P857

[4] A CONVENIENT METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF 3-PHENYL-1-ALKYNES [J].

CAPORUSSO, AM ;

POLIZZI, C ;

LARDICCI, L .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (17) :3920-3923

[5] CHIRAL ACETYLENES AS SYNTHETIC INTERMEDIATES .4. SYNTHESIS AND CHIROPTICAL PROPERTIES OF OPTICALLY-ACTIVE ALPHA,BETA-ACETYLENIC KETONES [J].

GIACOMELLI, G ;

ROSINI, C ;

CAPORUSSO, AM ;

PALLA, F .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (25) :4887-4891

[6] PREPARATION AND REACTIONS OF POLYFUNCTIONAL ORGANOZINC REAGENTS IN ORGANIC-SYNTHESIS [J].

KNOCHEL, P ;

SINGER, RD .

CHEMICAL REVIEWS, 1993, 93 (06) :2117-2188

[7] REACTION OF 1-BROMO-1,2-DIENES WITH ALKYLCUPRATES AS A REGIOSELECTIVE AND STEREOSELECTIVE ROUTE TO ACETYLENIC OR ALLENIC COMPOUNDS [J].

POLIZZI, C ;

CONSOLONI, C ;

LARDICCI, L ;

CAPORUSSO, AM .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 417 (1-2) :289-304

[8]

Stang P.J., 1995, MODERN ACETYLENE CHE

[9] PERMETHYLATED BETA-CYCLODEXTRIN AS CHIRAL SOLVATING AGENT FOR THE NMR ASSIGNMENT OF THE ABSOLUTE-CONFIGURATION OF CHIRAL TRISUBSTITUTED ALLENES [J].

UCCELLOBARRETTA, G ;

BALZANO, F ;

CAPORUSSO, AM ;

IODICE, A ;

SALVADORI, P .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) :2227-2231