zinc enolate
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Catalysts ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 1177
Author(s):  
Junma Ma ◽  
Takumi Suzuki ◽  
Satoru Kuwano ◽  
Takayoshi Arai

A PyBidine-Zn(OAc)2 complex catalyzed asymmetric chlorination of β-ketoesters. With assistance of NaHCO3, a newly developed N-pentafluorobenzyl-PyBidine (N-PFB-PyBidine)-Zn(OAc)2 catalyst promoted the reaction of α-benzyl-β-ketoesters with N-chlorosuccinimide (NCS) to give the chlorinated products with up to 82% ee. Results of a mechanistic study suggested that zinc-enolate of β-ketoesters was formed on the basic (N-PFB-PyBidine)-Zn(OAc)2 catalyst. The α-chlorinated-β-ketoester was successfully transformed into the chiral epoxide through sequential asymmetric chlorination/cyano-epoxidation in a one-pot synthesis.


2019 ◽  
Vol 60 (42) ◽  
pp. 151148
Author(s):  
Tetsuya Tsujihara ◽  
Moriho Tomeba ◽  
Shigeaki Ohkubo-Sato ◽  
Kyoko Iwabuchi ◽  
Rino Koie ◽  
...  

Tetrahedron ◽  
2015 ◽  
Vol 71 (46) ◽  
pp. 8830-8837 ◽  
Author(s):  
Ryosuke Haraguchi ◽  
Zenichi Ikeda ◽  
Akihiro Ooguri ◽  
Seijiro Matsubara

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