A novel method for the construction of (Z,E)- or (Z,Z)-conjugated alkadienyl carboxylates

被引：9

作者：

He, R ^{[1
]}

Deng, MZ ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 16期

关键词：

D O I：

10.1021/ol026286p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The stereocontrolled dehydrobromination of 1,2-dibromoethyl carboxylates giving (Z)-2-bromovinyl carboxylates could readily be approached by using DBU and a catalytic amount of hydroquinone as a base at -78 degreesC. The first investigation on the Suzuki-type cross-coupling of (2)-2-bromovinyl carboxylates as electrophiles with stereodefined alkenylboronic acids provides a novel method for the construction of (Z,E)or (Z,Z)-conjugated alkadienyl carboxylate moieties, which are often present in a range of natural products.

引用

页码：2759 / 2762

页数：4

共 24 条

[1] THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF ENOL ACETATES OF ALPHA-BROMO KETONES WITH 1-ALKENYLBORON, ARYLBORON, OR ALKYLBORON COMPOUNDS - A FACILE SYNTHESIS OF KETONES AND THEIR ENOL ACETATES [J].

ABE, S ;

MIYAURA, N ;

SUZUKI, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (10) :2863-2865

[2] APPROACHES TO AVERMECTIN ASSEMBLY - A CONCISE STEREOSPECIFIC SYNTHESIS OF THE HEXAHYDROBENZOFURAN ENTITY [J].

BARRETT, AGM ;

BARTA, TE ;

FLYGARE, JA ;

SABAT, M ;

SPILLING, CD .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) :2409-2414

[3]

BECHER J, 1980, SYNTHESIS-STUTTGART, P589

[4] A STEREOSPECIFIC SYNTHESIS OF CONJUGATED (E,Z)-ALKADIENES AND (E,E)-ALKADIENES BY THE PALLADIUM-CATALYZED REACTION OF (E)-1-ALKENYLBORONIC ACIDS AND 1-ALKENYL IODIDES [J].

CASSANI, G ;

MASSARDO, P ;

PICCARDI, P .

TETRAHEDRON LETTERS, 1983, 24 (24) :2513-2516

[5]

CECCHI R, 1984, GAZZ CHIM ITAL, V114, P225

[6] A novel stereocontrolled synthesis of 1,2-trans cyclopropyl ketones via Suzuki-type coupling of acid chlorides with cyclopropylboronic acids [J].

Chen, H ;

Deng, MZ .

ORGANIC LETTERS, 2000, 2 (12) :1649-1651

[7] A highly selective synthesis of diarylethynes and their oligomers by a palladium-catalyzed Sonogashira coupling reaction under phase transfer conditions [J].

Chow, HF ;

Wan, CW ;

Low, KH ;

Yeung, YY .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1910-1913

[8] TOTAL SYNTHESIS OF COLNELEIC ACID [J].

COREY, EJ ;

WRIGHT, SW .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1670-1673

[9] Powerful control by organoruthenium catalysts of the regioselective addition to C(1) or C(2) of the prop-2-ynyl ethers CC triple bond [J].

Doucet, H ;

Derrien, N ;

Kabouche, Z ;

Bruneau, C ;

Dixneuf, PH .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 551 (1-2) :151-157

[10]

FURSTENBERGER G, 1977, TETRAHEDRON LETT, P925, DOI 10.1016/S0040-4039(01)92793-5

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