Acyclic stereoselection. 47. Stereochemistry of the Michael addition of ester and ketone enolates to .alpha.,.beta.-unsaturated ketones

1990 ◽  
Vol 55 (1) ◽  
pp. 157-172 ◽  
Author(s):  
David A. Oare ◽  
Clayton H. Heathcock
Keyword(s):  
Michael Addition ◽  
Unsaturated Ketones ◽  
Ketone Enolates ◽  
Alpha Beta ◽  
The Michael Addition

Stereochemistry in the Michael addition of silylcuprate to .alpha.,.beta.-unsaturated sulfoxide

1989 ◽  
Vol 54 (1) ◽  
pp. 58-62 ◽  
Author(s):  
Ken Takaki ◽  
Toshihiro Maeda ◽  
Mitsuo Ishikawa
Keyword(s):  
Michael Addition ◽  
Alpha Beta ◽  
The Michael Addition

On the Stereoselectivity of the (-)-Dimenthyl Malonate Addition to α,β-Unsaturated Ketones

1996 ◽  
Vol 61 (12) ◽  
pp. 1805-1814 ◽  
Author(s):  
Ľubomír Šebo ◽  
Juraj Alföldi ◽  
Grety Rihs ◽  
Štefan Toma
Keyword(s):  
Michael Addition ◽  
Pure State ◽  
Nmr Spectra ◽  
Reaction Products ◽  
X Ray ◽  
Unsaturated Ketones ◽  
H Nmr ◽  
The Michael Addition

The Michael addition of (-)-dimenthyl malonate to eight α,β-unsaturated ketones has been studied. The ratio of diastereomers was calculated on the basis of the 1H NMR spectra of the crude reaction products. The diastereomer excess varied from 10 to 50%, depending on the structure of the starting enone. The pure diastereomer produced by addition of (-)-dimenthyl malonate to 2-benzylidene-1,4-indandione was isolated by repeated crystallization. X-ray analysis has shown that the isomer is (-)-dimenthyl (R)-2-[1-(1,3-dioxoindan-2-yl)-1-phenylmethyl]malonate (5a). The predominating diastereomers of (-)-dimenthyl(3-ferrocenyl-3-oxophenylpropyl)malonate (1a) and (-)-dimenthyl-2-(1-(1,3-dioxo[3]ferrocenophan-2-yl)-1-phenyl malonate (6a) were also isolated in pure state by careful crystallization.

Ionic-liquid-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene — An efficient and recyclable organocatalyst for Michael addition to α,β-unsaturated ketones

2012 ◽  
Vol 90 (3) ◽  
pp. 290-297 ◽  
Author(s):  
Manoj Kumar Muthyala ◽  
Bhupender S Chhikara ◽  
Keykavous Parang ◽  
Anil Kumar
Keyword(s):  
Ionic Liquid ◽  
Michael Addition ◽  
Room Temperature ◽  
Significant Loss ◽  
Unsaturated Ketones ◽  
Ability To Act ◽  
Solvent Free Conditions ◽  
Active Methylene Compounds ◽  
Active Methylene ◽  
The Michael Addition

A novel ionic-liquid-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene (IL–TBD) was synthesized and investigated for its ability to act as an active organocatalyst in the Michael addition of active methylene compounds and thiophenols to chalcones under solvent-free conditions. The IL–TBD afforded Michael addition products in excellent yields (82%–94%) at room temperature, and it was simply recycled and reused at least five times without significant loss of catalytic activity.

The Michael Addition of Indoles to α,β-Unsaturated Ketones Catalyzed by CeCl3×7H2O—NaI Combination Supported on Silica Gel.

ChemInform ◽  
2003 ◽  
Vol 34 (39) ◽  
Author(s):  
Giuseppe Bartoli ◽  
Massimo Bartolacci ◽  
Marcella Bosco ◽  
Gioia Foglia ◽  
Arianna Giuliani ◽  
...  
Keyword(s):  
Silica Gel ◽  
Michael Addition ◽  
Unsaturated Ketones ◽  
The Michael Addition

scholarly journals Enantioselective Michael addition of malonates to α,β-unsaturated ketones catalyzed by 1,2-diphenylethanediamine

RSC Advances ◽  
2018 ◽  
Vol 8 (73) ◽  
pp. 41699-41704
Author(s):  
Wei Wang ◽  
Ling Ye ◽  
Zhichuan Shi ◽  
Zhigang Zhao ◽  
Xuefeng Li
Keyword(s):  
Michael Addition ◽  
Unsaturated Ketones ◽  
The Michael Addition

1,2-Diphenylethanediamine could be directly utilized to promote the Michael addition of malonates and β-ketoesters to various α,β-unsaturated ketones.

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