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Chemistry
; 23(55): 13754-13759, 2017 Oct 04.
Article
in English
| MEDLINE
| ID: mdl-28786148
ABSTRACT
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.