Asymmetric Michael Reaction Catalyzed by Proline Lithium Salt: Efficient Synthesis ofL-Proline and Isoindoloisoquinolinone Derivatives

2013 ◽  
Vol 19 (11) ◽  
pp. 3573-3578 ◽  
Author(s):  
Kun Xu ◽  
Sheng Zhang ◽  
Yanbin Hu ◽  
Zhenggen Zha ◽  
Zhiyong Wang
Keyword(s):  
Michael Reaction ◽  
Lithium Salt ◽  
Efficient Synthesis ◽  
Asymmetric Michael Reaction

scholarly journals Multistep batch-flow hybrid synthesis of a terbinafine precursor

2021 ◽  
Author(s):  
Tamás Hergert ◽  
Béla Mátravölgyi ◽  
Róbert Örkényi ◽  
János Éles ◽  
Ferenc Faigl
Keyword(s):  
Methyl Ether ◽  
Lithium Salt ◽  
Scale Up ◽  
Hybrid Process ◽  
High Yield ◽  
Grignard Reaction ◽  
Efficient Synthesis ◽  
Synthetic Process ◽  
Synthesis Route ◽  
Selective Addition

AbstractA three-step batch-flow hybrid process has been developed for an expeditious synthesis of the enynol key intermediate of antifungal terbinafine. This procedure involves consecutive organometallic steps without the necessity of any in-line purification: after a metalation by n-butyllithium, a selective addition of the lithium salt was elaborated followed by a Grignard reaction resulting in a high yield of 6,6-dimethylhept-1-en-4-yn-3-ol. Moreover, as an alternative to tetrahydrofuran, cyclopentyl methyl ether was used as solvent implementing a safe, sustainable, yet selective synthetic process. Even on a laboratory-scale, the optimized batch-flow hybrid process had a theoretical throughput of 41 g/h. Furthermore, the newly developed process provides an efficient synthesis route to the key-intermediate, while making acrolein obsolete, minimizing side-products, and enabling safe and convenient scale-up.

ChemInform Abstract: High Diastereoselectivity Induced by a Fluorous Alkyl Group in the Asymmetric Michael Reaction of Nitroalkenes Catalyzed by a Prolinol Methyl Ether.

ChemInform ◽  
2014 ◽  
Vol 45 (18) ◽  
pp. no-no
Author(s):  
Kazumasa Funabiki ◽  
Masaya Ohta ◽  
Yuta Sakaida ◽  
Kiyofumi Oida ◽  
Yasuhiro Kubota ◽  
...  
Keyword(s):  
Methyl Ether ◽  
Alkyl Group ◽  
Michael Reaction ◽  
Asymmetric Michael Reaction

Cationic [2,6-Bis(2‘-oxazolinyl)phenyl]palladium(II) Complexes:  Catalysts for the Asymmetric Michael Reaction

2000 ◽  
Vol 19 (7) ◽  
pp. 1282-1291 ◽  
Author(s):  
Mark A. Stark ◽  
Geraint Jones ◽  
Christopher J. Richards
Keyword(s):  
Michael Reaction ◽  
Asymmetric Michael Reaction

2-Azanorbornane-Based Amino Alcohol Organocatalysts for Asymmetric Michael Reaction of β-Keto Esters with Nitroolefins

2019 ◽  
Vol 2019 (24) ◽  
pp. 3882-3889 ◽  
Author(s):  
Rei Togashi ◽  
Madhu Chennapuram ◽  
Chigusa Seki ◽  
Yuko Okuyama ◽  
Eunsang Kwon ◽  
...  
Keyword(s):  
Amino Alcohol ◽  
Michael Reaction ◽  
Keto Esters ◽  
Asymmetric Michael Reaction

Asymmetric Michael reaction between aldehydes and nitroalkanes promoted by pyrrolidine-containing C2-symmetric organocatalysts

2019 ◽  
Vol 68 (7) ◽  
pp. 1402-1406
Author(s):  
K. A. Bykova ◽  
A. A. Kostenko ◽  
A. S. Kucherenko ◽  
S. G. Zlotin
Keyword(s):  
Michael Reaction ◽  
Asymmetric Michael Reaction
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