Rapid assembly of structurally defined and highly functionalized conjugated dienes via tethered enyne metathesis

被引：40

作者：

Yao, QW ^{[1
]}

机构：

[1] No Illinois Univ, Michael Faraday Labs, Dept Chem & Biochem, De Kalb, IL 60115 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 13期

关键词：

D O I：

10.1021/ol016026s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Conjugated dienes are versatile building blocks in organic synthesis, and the development of new methods for their synthesis remains an important topic in modern synthetic organic chemistry. We describe here an expedient synthesis of highly functionalized conjugated dienes through sequential silicon-tethered ring-closing enyne metathesis mediated by Grubbs' Ru carbene catalysts and Tamao oxidation. Notable attributes of this methodology include short synthetic manipulations and the structural complexity it confers on the resulting diene moiety.

引用

页码：2069 / 2072

页数：4

共 56 条

[1] Ackermann L, 2001, SYNLETT, P397
[2] Armstrong SK, 1998, J CHEM SOC PERK T 1, P371
[3] NOVEL STEREOSPECIFIC ALKENYL-ALKENYL CROSS-COUPLING BY A PALLADIUM-CATALYZED OR NICKEL-CATALYZED REACTION OF ALKENYLALANES WITH ALKENYL HALIDES
BABA, S
NEGISHI, E
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (21) : 6729 - 6731
[4] The heck reaction as a sharpening stone of palladium catalysis
Beletskaya, IP
Cheprakov, AV
[J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
[5] Formation of dissymmetric eight-membered silalketals by ring-closing metathesis and their conversion to spiroketals
Boiteau, JG
Van de Weghe, P
Eustache, J
[J]. TETRAHEDRON LETTERS, 2001, 42 (02) : 239 - 242
[6] SILICON-TETHERED REACTIONS
BOLS, M
SKRYDSTRUP, T
[J]. CHEMICAL REVIEWS, 1995, 95 (05) : 1253 - 1277
[7] Brase S, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P99
[8] Improvement in olefin metathesis using a new generation of ruthenium catalyst bearing an imidazolylidene ligand: Synthesis of heterocycles
Briot, A
Bujard, M
Gouverneur, V
Nolan, SP
Mioskowski, C
[J]. ORGANIC LETTERS, 2000, 2 (11) : 1517 - 1519
[9] Carruthers W, 1990, Cycloaddition Reactions in Organic Synthesis
[10] Cassidy JH, 1997, SYNLETT, P1411

← 1 2 3 4 5 6 →