Stereoselective Synthesis of Dihydrocoumarins via [1,2]-Phospha-Brook Rearrangement in Three-Component Coupling Reaction of α-Ketoesters, o-Quinone Methides, and Dialkyl Phosphites

Author(s):  
Ravneet Kaur ◽  
Dipak Singh ◽  
Ravi P. Singh
2016 ◽  
Vol 14 (20) ◽  
pp. 4704-4711 ◽  
Author(s):  
Azusa Kondoh ◽  
Masahiro Terada

A three-component coupling reaction of α-ketoesters, imines, and diethyl phosphite under Brønsted base catalysis was developed by utilizing the [1,2]-phospha-Brook rearrangement.


RSC Advances ◽  
2021 ◽  
Vol 11 (22) ◽  
pp. 13097-13104
Author(s):  
Makoto Shimizu ◽  
Asako Higashino ◽  
Isao Mizota ◽  
Yusong Zhu

Treatment of α-aldimino thioesters with dialkylzinc reagents in the presence of aldehydes or imines gives three-component coupling products in good yields with good to high anti-selectivities.


1995 ◽  
Vol 60 (6) ◽  
pp. 1834-1840 ◽  
Author(s):  
Naoto Chatani ◽  
Nobuyoshi Amishiro ◽  
Takaya Morii ◽  
Toshiaki Yamashita ◽  
Shinji Murai

2004 ◽  
Vol 6 (22) ◽  
pp. 4049-4051 ◽  
Author(s):  
Hiroto Yoshida ◽  
Masahiko Watanabe ◽  
Hiroyuki Fukushima ◽  
Joji Ohshita ◽  
Atsutaka Kunai

2011 ◽  
Vol 7 ◽  
pp. 1334-1341 ◽  
Author(s):  
Sanny Verma ◽  
Suman L Jain ◽  
Bir Sain

PEG-embedded potassium tribromide ([K+PEG]Br3 −) was found to be an efficient and recyclable catalyst for the synthesis of functionalized piperidines in high yields in a one step, three component coupling between aldehyde, amine and β-keto ester. At the end of the reaction the [K+PEG]Br3 − was readily regenerated from the reaction mixture by treating the residue containing [K+PEG]Br− with molecular bromine.


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