Allenols versus Allenones: Rhodium-Catalyzed Regiodivergent and Tunable Allene Reactivity with Triazoles

被引：13

作者：

Alcaide, Benito ^{[1
]}

Almendros, Pedro ^{[2
]}

Cembellin, Sara ^{[1
]}

Martinez del Campo, Teresa ^{[1
]}

Palop, Guillermo ^{[1
]}

机构：

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

[2] CSIC, IQOG, Juan Cierva 3, Madrid 28006, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 55期

关键词：

allenes; enones; heterocycles; regioselectivity; synthetic methods; GOLD CATALYSIS; CYCLIZATION; KETONES; CYCLOISOMERIZATION/DIMERIZATION; DIMERIZATION; ACTIVATION; GOLD(III); SILVER; FURANS; BONDS;

D O I：

10.1002/chem.201702468

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2-Pyrrolines and 6-oxo-hexa-2,4-dienals have been prepared through the divergent reactions of 1-benzenesulfonyl-4-aryl-1,2,3-triazoles with functionalized allenes. The rhodium-catalyzed reactions between allenols and 1-benzenesulfonyl-4-aryl-1,2,3-triazoles yielded 2-pyrrolines. This transformation is compatible with the presence of aliphatic, aromatic, heterocyclic, amide, and halogen functional groups. Interestingly, a reactivity switch took place when the allene-tethered alcohol substrate was replaced by its ketone counterpart. When the rhodium-catalyzed reaction of 1-benzenesulfonyl-4-phenyl-1,2,3-triazole was performed with allenones, acyclic 6-oxo-hexa-2,4-dienals were stereoselectively formed as (2Z,4E) isomers.

引用

页码：13754 / 13759

页数：6

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