Controlled Heterocyclization/Cross-Coupling Domino Reaction of β,γ-Allendiols and α-Allenic Esters: Method and Mechanistic Insight for the Preparation of Functionalized Buta-1,3-dienyl Dihydropyrans

被引：9

作者：

Alcaide, Benito ^{[1
]}

Almendros, Pedro ^{[2
]}

Martinez del Campo, Teresa ^{[1
]}

Teresa Quiros, M. ^{[1
]}

Soriano, Elena ^{[2
]}

Marco-Contelles, Jose L. ^{[2
]}

机构：

[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, Grp Lactamas & Heterociclos Bioact,CSIC,Unidad As, E-28040 Madrid, Spain

[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 42期

关键词：

allenes; density functional calculations; palladium; reaction mechanisms; regioselectivity; PALLADIUM-CATALYZED CYCLOISOMERIZATION/DIMERIZATION; EFFICIENT SYNTHESIS; CYCLIZATION REACTION; 2,3-ALLENOIC ACIDS; ASYMMETRIC-SYNTHESIS; GOLDEN OPPORTUNITIES; DENSITY FUNCTIONALS; 1,2-ALLENYL KETONES; GAMMA-ALLENOLS; PD;

D O I：

10.1002/chem.201300774

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Starting from ,-allendiols and -allenic acetates, a chemo- and regiocontrolled palladium-catalyzed methodology has provided access to enantiopure 3,6-dihydropyrans that bear a buta-1,3-dienyl moiety. Thus, it has been demonstrated for the first time that the preparation of six-membered heterocycles through cross-coupling reactions of two different allenes can be accomplished. These heterocyclization/cross-coupling reactions have been developed experimentally and their mechanisms have additionally been investigated by a computational study.

引用

页码：14233 / 14244

页数：12

共 126 条

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