Stereoselective Synthesis of Trisubstituted Vinylboronates from Ketone Enolates Triggered by 1,3‐Metalate Rearrangement of Lithium Enolates

2019 ◽  
Vol 58 (44) ◽  
pp. 15813-15818 ◽  
Author(s):  
Yue Hu ◽  
Wei Sun ◽  
Tao Zhang ◽  
Nuo Xu ◽  
Jianeng Xu ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Lithium Enolates ◽  
Ketone Enolates

Stereoselective Synthesis of Trisubstituted Vinylboronates from Ketone Enolates Triggered by 1,3‐Metalate Rearrangement of Lithium Enolates

2019 ◽  
Vol 131 (44) ◽  
pp. 15960-15965 ◽  
Author(s):  
Yue Hu ◽  
Wei Sun ◽  
Tao Zhang ◽  
Nuo Xu ◽  
Jianeng Xu ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Lithium Enolates ◽  
Ketone Enolates

scholarly journals Stereoselective Synthesis of Vinylcyclopropanes from 2-Phenylsulfonyl-1,3-cyclohexadienes and Ketone Enolates or Nitrile Anion.

1994 ◽  
Vol 48 ◽  
pp. 252-257 ◽  
Author(s):  
Anna M. Ericsson ◽  
Niklas A. Plobeck ◽  
Jan-E. Bäckvall ◽  
Clara Viñas ◽  
Jose A. Ayllón ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Ketone Enolates

Synthèse stéréosélective de (±) boschnialactone, (±) 7-épiteucriumlactone et (±) 7-épiisoiridomyrmécine. Étude de la stéréochimie par spectroscopie de résonance magnétique nucléaire

1990 ◽  
Vol 68 (4) ◽  
pp. 620-627 ◽  
Author(s):  
B. Hanquet ◽  
B. Tabyaoui ◽  
J.-C. Caille ◽  
M. Farnier ◽  
R. Guilard
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Structural Analysis ◽  
Nucleophilic Addition ◽  
Stereoselective Synthesis ◽  
Magnetic Resonance Data ◽  
Lithium Enolates ◽  
Resonance Data ◽  
Résonance Magnétique ◽  
Stereoselective Syntheses ◽  
C Nmr

The stereoselective syntheses of (±) boschnialactone 1, (±) 7-epiteucriumlactone 2, and (±) 7-epiisoiridomyrmecine 3 are described. Their preparation involved Stetter's reaction followed by nucleophilic addition of lithium enolates of suitable esters. Silylated reagents are used in the lactonisation step and the observed yields are between 63 and 78%. The proposed structural analysis is not in accord with the results of a previous study. The nuclear magnetic resonance data are determined using ID and 2D proton and carbon NMR experiments. Keywords: stereoselective synthesis, boschnialactone, 7-epiteucriumlactone, 7-epiisoiridomyrmecine, 1H and 13C NMR.

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