Stereocontrolled Synthesis of a Cn-Cn+6Building Block for the Unnatural Enantiomers of Important Polyol,Polyene Antibiotics from an Epoxy Alcohol by a Reduction/Conjugate Addition/Hydroxylation Sequence

2013 ◽  
Vol 2013 (29) ◽  
pp. 6563-6583 ◽  
Author(s):  
Rainer Kramer ◽  
Reinhard Brückner
Keyword(s):  
Conjugate Addition ◽  
Polyene Antibiotics ◽  
Epoxy Alcohol ◽  
Stereocontrolled Synthesis

A Facile and Stereocontrolled Synthesis of γ-Substituted γ-Fluoroglutamates by Conjugate Addition: Conflicting Effect between Fluorinated Enaminoester and Hinderered Michael Acceptor

2010 ◽  
Vol 75 (22) ◽  
pp. 7596-7604 ◽  
Author(s):  
Emmanuelle Drège ◽  
Anaïs Guillaume ◽  
Nadjia Boukhedimi ◽  
Jérôme Marrot ◽  
Claire Troufflard ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Stereocontrolled Synthesis ◽  
Michael Acceptor

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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