Synthesis of spirocyclic heterocycles from α,β-unsaturated N-acyliminium ions

2021 ◽  
Vol 19 (1) ◽  
pp. 259-272
Author(s):  
Thanphat Thaima ◽  
Arife Yazici ◽  
Chiramet Auranwiwat ◽  
Anthony C. Willis ◽  
Uta Wille ◽  
...  
Keyword(s):  
Acyliminium Ions

The reactions of α,β-unsaturated N-acyliminium ions, generated in situ from 4(S)-O-substitutedhydroxy-5-hydroxy-5-vinyl-N-alkylpyrrolidin-2-ones, with allylsilanes and indoles leading to the formation of spirocyclic heterocycles, are reported.

Synthesis of 5-Substituted 2-Pyrrolidinones by Coupling of Organozinc Reagents with Cyclic N-Acyliminium Ions

Synthesis ◽  
2019 ◽  
Vol 51 (24) ◽  
pp. 4650-4656
Author(s):  
Ivann Zaragoza-Galicia ◽  
Zaira A. Santos-Sánchez ◽  
Yazmín I. Hidalgo-Mercado ◽  
Horacio F. Olivo ◽  
Moisés Romero-Ortega
Keyword(s):  
Diethyl Ether ◽  
Boron Trifluoride ◽  
Titanium Tetrachloride ◽  
Reaction Medium ◽  
Coupling Reaction ◽  
Acyliminium Ions ◽  
Organozinc Reagents ◽  
Ether Complex ◽  
Organozinc Reagent

A coupling reaction between cyclic N-acyliminium ions with organozinc reagents is described. The cyclic N-acyliminium ions, generated in situ from N-substituted-5-hydroxy-2-pyrrolidinones by treatment with boron trifluoride–diethyl ether complex or titanium tetrachloride, are trapped by the organozinc reagent, which is formed from an alkyl bromide in the presence of zinc in the same reaction medium. The N-substituted-5-allyl-2-pyrrolidinones generated using this method serve as versatile intermediates for the synthesis of azabicyclic systems with indolizidine and pyrroloazepinolizidine cores.

scholarly journals Catalytic Asymmetric Additions of Enol Silanes to in situ Generated Cyclic, Aliphatic N‐Acyliminium Ions

2021 ◽  
Author(s):  
Benjamin List ◽  
Oleg Grossmann ◽  
Rajat Maji ◽  
Miles H. Aukland ◽  
Sunggi Lee
Keyword(s):  
Acyliminium Ions ◽  
Catalytic Asymmetric ◽  
Asymmetric Additions
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