Chiral amines as organocatalysts for asymmetric conjugate addition to nitroolefins and vinyl sulfones via enamine activation

2007 ◽  
pp. 3123 ◽  
Author(s):  
Sarah Sulzer-Mossé ◽  
Alexandre Alexakis
Keyword(s):  
Conjugate Addition ◽  
Chiral Amines

scholarly journals Indolyl substituted 4-oxobut-2-enoic acids. Synthesis and aza-Michael additions

2007 ◽  
Vol 5 (3) ◽  
pp. 688-705 ◽  
Author(s):  
Dušan Berkeš ◽  
Anna Koren̆ová ◽  
Peter Šafár̆ ◽  
Helena Horváthová ◽  
Nadežda Prónayová
Keyword(s):  
Conjugate Addition ◽  
Enoic Acid ◽  
Chiral Amines ◽  
Indole Ring ◽  
Michael Additions ◽  
Michael Acceptors ◽  
Asymmetric Transformation

AbstractThe synthesis of three new substituted 4-hetereoaryl-4-oxobut-2-enoic acids with indole ring substitutedin positions 3-, 5- and 7- is described. The addition of these Michael acceptors to 4-(1-phenylsulphonylpyrrol-3-yl)-4-oxobut-2-enoic acid in conjugate addition was explored using both racemic and chiral amines. In tandem with the crystallization-induced asymmetric transformation (CIAT) protocol the effective methodology for the synthesis of enantiomerically highly enriched substituted 2-amino-4-heteroaryl-4-oxobutanoic acids as multifunctional homotryptophan analogues was developed.

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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