Domino 1,4- and 1,6-Addition Reactions of Ketene Silyl Acetals to Dialkynyl Imines Promoted by Aluminum Chloride: Synthesis of Multifunctionalized β-Lactams

2019 ◽  
Vol 84 (22) ◽  
pp. 14770-14794 ◽  
Author(s):  
Iwao Hachiya ◽  
Kenta Nakamura ◽  
Masaya Hara ◽  
Koki Sato ◽  
Makoto Shimizu
Keyword(s):  
Aluminum Chloride ◽  
Addition Reactions ◽  
Silyl Acetals

Integrated reactions using addition to conjugated imines and iminium salts

2012 ◽  
Vol 84 (12) ◽  
pp. 2609-2617 ◽  
Author(s):  
Takafumi Nishi ◽  
Isao Mizota ◽  
Makoto Shimizu
Keyword(s):  
Nucleophilic Addition ◽  
Claisen Rearrangement ◽  
Functional Materials ◽  
Addition Reactions ◽  
Iminium Salts ◽  
Silyl Acetals ◽  
Imino Esters

Recently, nucleophilic addition reactions to imino functions have been utilized in many crucial steps for the synthesis of bioactive and functional materials. This article summarizes the integrated “umpolung” reactions of α-imino esters and the use of iminium salts as reactive electrophiles. Regarding the umpolung reactions, the following five reactions are discussed: (1) N-alkylation/homocoupling; (2) tandem N-ethylation/C-allylation; (3) tandem N-ethylation/C-cyanation; (4) reduction of imines with tris(trimethylsilyl)aluminum; and (5) N-alkylation and Claisen rearrangement. Moreover, the generation and reactions of alkoxycarbonyl iminium species are also discussed. These are prepared easily from trisubstituted amino ketene silyl acetals by oxidation, and the subsequent nucleophilic addition of various nucleophiles readily affords the addition products.

scholarly journals Preparation and facile addition reactions of iminium salts derived from amino ketene silyl acetal and amino silyl enol ether

RSC Advances ◽  
2020 ◽  
Vol 10 (46) ◽  
pp. 27874-27883
Author(s):  
Makoto Shimizu ◽  
Shingo Hata ◽  
Koichi Kondo ◽  
Kazuhiro Murakami ◽  
Isao Mizota ◽  
...  
Keyword(s):  
Addition Reactions ◽  
Amino Ketone ◽  
Enol Ether ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Iminium Salts ◽  
Silyl Enol Ether ◽  
Silyl Acetals

While iminium salts generated from amino ketene silyl acetals react with silyl enol ethers, those from amino silyl enol ethers also undergo facile addition reactions to give alpha-amino ketone derivatives in good yields.

Thia-Michael Addition Reactions in Water Using 3-[Bis(Alkylthio) Methylene] Pentane-2,4-Diones as Odorless and Efficient Thiol Equivalents

2007 ◽  
Vol 4 (4) ◽  
pp. 281-284 ◽  
Author(s):  
Yanyan Chai ◽  
Dewen Dong ◽  
Yan Ouyang ◽  
Yongjiu Liang ◽  
Yan Wang ◽  
...  
Keyword(s):  
Michael Addition ◽  
Addition Reactions
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