Reactions of Enaminones with Diazocarbonyl Compounds

The [Cu(acac)2]‐catalyzed reactions of several tertiary enaminones with three diazocarbonyl compounds, i.e., dimethyl diazomalonate, ethyl diazoacetoacetate, and ethyl diazoacetate, yielded amino‐ and additionally carbonyl‐substituted dihydrofurans, together with further furan derivatives. Due to th...

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Bibliographic Details
Published in:	Helvetica chimica acta Vol. 96; no. 3; pp. 488 - 493
Main Authors:	SeymaGüngör, Füsun, Hanciolu, Neslihan, Anaç, Olcay
Format:	Journal Article
Language:	English
Published:	Zürich WILEY-VCH Verlag 01-03-2013 WILEY‐VCH Verlag Wiley Subscription Services, Inc
Subjects:	Carbenoids Diazo compounds dihydro Electrocyclic reactions Enaminones Furans Furans, dihydro
Online Access:	Get full text
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Summary:	The [Cu(acac)2]‐catalyzed reactions of several tertiary enaminones with three diazocarbonyl compounds, i.e., dimethyl diazomalonate, ethyl diazoacetoacetate, and ethyl diazoacetate, yielded amino‐ and additionally carbonyl‐substituted dihydrofurans, together with further furan derivatives. Due to the conjugation of α‐carbonyl/α‐Ph groups, reactions proceeded only via 1,5‐electrocyclization of corresponding keto‐ylides. On the other hand, in the absence of any α‐substituent, tertiary enaminone and ethyl diazoacetate, reacted via an accompanying mechanism by a push‐pull cyclopropane intermediate, to yield a 2,4‐dicarbonyl‐substituted furan in one step with moderate yield.
Bibliography:	ark:/67375/WNG-KJ3DD74B-N ArticleID:HLCA201200233 istex:A8436CCE5F04048E2FBAB9F05CF4947687A44CDF ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 23
ISSN:	0018-019X 1522-2675
DOI:	10.1002/hlca.201200233