β‑Aryl-α-nitro-α,β-enals as Heterodienes and Dienophiles

As demonstrated with the β-(2-furyl)-substituted analogue 1b, β-aryl-α-nitro-α,β-enals (1) behave as heterodienes against enamines and enol ethers using their enal unit (e.g., 1b → 12). α-Nitro-α,β-enals can act as well as highly reactive dienophiles to render adducts endowed with nitrogenated quate...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 79; no. 18; pp. 8645 - 8651
Main Authors Lago-Santomé, Hugo, Martínez-Bescos, Patricia, Fernández-González, Marta, Ozores-Viturro, Lidia, Cagide-Fagín, Fernando, Alonso, Ricardo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.09.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
enamines
enol ethers
organic chemistry
Physical Sciences
Science & Technology
ACID
ANNULATION
ANALOGS
CONVERGENT APPROACH
Online AccessGet full text
ISSN0022-3263
1520-6904
1520-6904
DOI10.1021/jo501418u

Cover

More Information
Summary:As demonstrated with the β-(2-furyl)-substituted analogue 1b, β-aryl-α-nitro-α,β-enals (1) behave as heterodienes against enamines and enol ethers using their enal unit (e.g., 1b → 12). α-Nitro-α,β-enals can act as well as highly reactive dienophiles to render adducts endowed with nitrogenated quaternary centers (e.g., 1b → 15a). A hetero-Diels–Alder (HDA)/Diels–Alder (DA) sequence from 1b also proved feasible on serial treatment with ethyl vinyl ether and Danishefsky’s diene (1b → 14).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/jo501418u