AlCl3-Promoted Facile E-to-Z Isomerization Route to (Z)-2-Methyl-1-buten-1,4-ylidene Synthons for Highly Efficient and Selective (Z)-Isoprenoid Synthesis

被引：17

作者：

Wang, Guangwei ^{[1
]}

Negishi, Ei-ichi ^{[1
]}

机构：

[1] Purdue Univ, Herbert C Brown Labs Chem, W Lafayette, IN 47907 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 11期

基金：

美国国家卫生研究院;

关键词：

Carboalumination; Zirconium; Isomerization; Stereoselectivity; Terpenoids; TRANSITION-METAL CATALYSIS; CARBON BOND FORMATION; CONTROLLED CARBOMETALATION; DERIVATIVES; ALCOHOLS; HALIDES; ALKYNES;

D O I：

10.1002/ejoc.200801188

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Zr-catalyzed methylalumination of 3-butyn-1-ols followed by AlCl3-promoted stereoisomerization at 50 degrees C for 6 h provides 4-iodo-3-methyl-3-buten-1-ols 2b and 6 (>= 98% Z configuration) in 87 and 67% yields, respectively. (Z)-1,4-Diiodo-2-methyl-1-butene (1b) obtainable by iodination of 2b is a valuable synthon for efficient and selective syntheses of (Z)-alkene-containing isoprenoids. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：1679 / 1682

页数：4

共 14 条

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SYNTHESIS-STUTTGART, 2008, (11): : 1703 - 1706
[3] HIGHLY STEREOSELECTIVE AND GENERAL-SYNTHESIS OF (Z)-3-METHYL-2-ALKEN-1-OLS VIA PALLADIUM-CATALYZED CROSS COUPLING OF (Z)-3-IODO-2-BUTEN-1-OL WITH ORGANOZINCS AND OTHER ORGANOMETALS
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TETRAHEDRON LETTERS, 1993, 34 (09) : 1437 - 1440
[4] A FACILE SYNTHESIS OF METHYL (2Z,5E)-6-ARYL-4,4-DICYANO-5-AZA-2,5-HEXADIENOATES [(1E,4Z)-2-AZA-1,4-PENTADIENES]
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[5] Stereoselective synthesis of (E)- and (Z)-3-hydroxy-2-methyl-1-alkenyl iodides by base-promoted ring-opening of iodomethylated epoxides
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TETRAHEDRON LETTERS, 2006, 47 (28) : 4843 - 4848
[6] Efficient Highly Selective Synthesis of Methyl 2-(Ethynyl)alk-2(E)-enoates and 2-(1′-Chlorovinyl)alk-2(Z)-enoates from 2-(Methoxycarbonyl)-2,3-allenols
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ORGANIC LETTERS, 2009, 11 (10) : 2169 - 2172
[7] Alkyl (E,Z)-2-(2-benzoyl-2-ethoxycarbonyl-1-ethenyl)amino-3-dimethylaminopropenoates in the synthesis of fused pyrimidinones. A facile route to 3-aminoazino-4H-pyrimidin-4-one
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Al Anshori, Jamaludin
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RSC ADVANCES, 2022, 12 (05) : 2972 - 2979
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J Org Chem, 6 (1863):

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