Conjugate Addition - SNAr Domino Reaction for the Synthesis of Benzo- or Pyridyl-Fused Lactams and Sultams

Synthesis ◽  
2010 ◽  
Vol 2010 (24) ◽  
pp. 4273-4281
Author(s):  
Karsten Juhl ◽  
Niels Nørager
Keyword(s):  
Conjugate Addition ◽  
Domino Reaction

scholarly journals First Zinc Bromide Promoted Annulative Domino Reactions between Enamines and Cyclic Morita–Baylis–Hillman Alcohols: Synthesis of N,O-Ketals

Synlett ◽  
2020 ◽  
Vol 31 (13) ◽  
pp. 1282-1286
Author(s):  
Farhat Rezgui ◽  
Ghalia Bouhalleb ◽  
Ahmed Meddeb ◽  
Noura Fakhar Bourguiba ◽  
Julien Legros ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Conjugate Addition ◽  
Domino Reaction ◽  
Domino Reactions ◽  
Zinc Bromide ◽  
Iminium Ion

A new efficient ZnBr2-mediated annulative domino reaction between enamines and cyclic Morita–Baylis–Hillman (MBH) alcohols is disclosed. The process involves a tandem sequence (intermolecular conjugate addition of enamines to MBH alcohols and intramolecular nucleophilic addition of the hydroxyl moiety to the transiently generated iminium ion), affording the corresponding N,O-ketals diastereoselectively in good yields.

Nickel and Cobalt-Catalyzed Coupling of Alkyl Halides with Alkenes via Heck Reactions and Radical Conjugate Addition

2013 ◽  
Vol 13 (6) ◽  
pp. 802-813 ◽  
Author(s):  
Qun Qian ◽  
Zhenhua Zang ◽  
Yang Chen ◽  
Weiqi Tong ◽  
Hegui Gong
Keyword(s):  
Conjugate Addition ◽  
Alkyl Halides ◽  
Heck Reactions

scholarly journals (2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol

Molbank ◽  
10.3390/m1140 ◽  
2020 ◽  
Vol 2020 (2) ◽  
pp. M1140
Author(s):  
Jack Bennett ◽  
Paul Murphy
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Ir Spectroscopy ◽  
13C Nmr ◽  
Conjugate Addition ◽  
13C Nmr Spectroscopy ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Esi Mass Spectrometry ◽  
The One

(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by 1H and 13C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.

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