Practical Synthesis and Reactivity of [3]Dendralene

被引：48

作者：

Bradford, Tanya A. ^{[1
]}

Payne, Alan D. ^{[1
]}

Willis, Anthony C. ^{[1
]}

Paddon-Row, Michael N. ^{[2
]}

Sherburn, Michael S. ^{[1
]}

机构：

[1] Australian Natl Univ, Res Sch Chem, Canberra, ACT 0200, Australia

[2] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 02期

基金：

澳大利亚研究理事会;

关键词：

DIELS-ALDER REACTIONS; CATIONIC OXAZABOROLIDINES; DENDRALENE FAMILY; 3-METHYLENE-1,4-PENTADIENE; CYCLOADDITIONS; HYDROCARBONS; CONJUGATION; EQUIVALENT; CATALYSIS; PYROLYSIS;

D O I：

10.1021/jo9024557

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient and high-yielding three-step synthesis of the simplest branched triene, [3]dendralene, has been devised. The synthesis is robust and operationally simple, requiring no chromatography and involving no protecting groups or specialized equipment, allowing the synthesis of the volatile hydrocarbon in pure, solvent free form on a multigram scale. The stability, dimerization when stored neat, and Diets-Alder reactivity of [3]dendralene-including double cycloaddition sequences and catalytic enantioselective variant-are reported.

引用

页码：491 / 494

页数：4

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