The Michael-type Reaction of B-Iodo-9-BBN/Ethoxyethyne Adduct to α,β-Unsaturated Ketones. A Selective Synthesis of δ-Keto Esters

1989 ◽  
Vol 18 (10) ◽  
pp. 1723-1726 ◽  
Author(s):  
Fumitoshi Kawamura ◽  
Takao Tayano ◽  
Yoshitaka Satoh ◽  
Shoji Hara ◽  
Akira Suzuki
Keyword(s):  
Selective Synthesis ◽  
Unsaturated Ketones ◽  
Type Reaction ◽  
Keto Esters

Selective Synthesis of β-Amino Esters and β-Lactams by Rhodium-Catalyzed Reformatsky-Type Reaction.

ChemInform ◽  
2003 ◽  
Vol 34 (11) ◽  
Author(s):  
Kazuo Kanai ◽  
Hitoshi Wakabayashi ◽  
Toshio Honda
Keyword(s):  
Selective Synthesis ◽  
Type Reaction ◽  
Amino Esters

scholarly journals Addition of dithi(ol)anylium tetrafluoroborates to α,β-unsaturated ketones

2018 ◽  
Vol 14 ◽  
pp. 515-522 ◽  
Author(s):  
Yu-Chieh Huang ◽  
An Nguyen ◽  
Simone Gräßle ◽  
Sylvia Vanderheiden ◽  
Nicole Jung ◽  
...  
Keyword(s):  
Room Temperature ◽  
Systematic Investigation ◽  
Chiral Auxiliary ◽  
Subsequent Reduction ◽  
Unsaturated Ketones ◽  
Type Reaction ◽  
Ketene Dithioacetals

In the presented study, dithi(ol)anylium tetrafluoroborates are added to α,β-unsaturated ketones in a Michael-type reaction yielding diverse substituted ketene diothi(ol)anes. The reactions proceed at room temperature in 1 or 13 h without the need of further additives. The presented procedure is in particular useful for dithi(ol)anylium tetrafluoroborates without electron-withdrawing groups in α-position. This is advantageous with respect to previous approaches, which were limited to the use of ketene dithioacetals substituted with electron-withdrawing groups. Aiming for the systematic investigation of possible steric and electronic influences on the outcome of the reaction, various combinations of electrophiles and nucleophiles were used and the results of the reactions were compared based on the type of the used dithioacetal. The scope of the presented procedure is shown with four additional transformations including the use of additional electrophiles and nucleophiles, the use of a chiral auxiliary and subsequent reduction of selected products. Additionally, we extended the reaction to the synthesis of diene dithiolanes by addition of an ynone to α-alkyl or aryl-substitued dithiolanylium TFBs.

Palladium-catalyzed conjugate addition type reaction of 5-iodopyrimidines with α,β-unsaturated ketones

1991 ◽  
Vol 28 (2) ◽  
pp. 509-512 ◽  
Author(s):  
Akimori Wada ◽  
Kazuhiro Ohki ◽  
Sotoo Nagai ◽  
Shōichi Kanatomo
Keyword(s):  
Conjugate Addition ◽  
Unsaturated Ketones ◽  
Type Reaction ◽  
Palladium Catalyzed

Selective synthesis of α-substituted β-keto esters from aldehydes and diazoesters on mesoporous silica catalysts

2008 ◽  
Vol 49 (32) ◽  
pp. 4788-4791 ◽  
Author(s):  
Hiroaki Murata ◽  
Haruro Ishitani ◽  
Masakazu Iwamoto
Keyword(s):  
Mesoporous Silica ◽  
Selective Synthesis ◽  
Keto Esters
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