Thiourea-Catalyzed Nucleophilic Addition of TMSCN and Ketene Silyl Acetals to Nitrones and Aldehydes.

ChemInform ◽  
2003 ◽  
Vol 34 (27) ◽  
Author(s):  
Tomotaka Okino ◽  
Yasutaka Hoashi ◽  
Yoshiji Takemoto
Keyword(s):  
Nucleophilic Addition ◽  
Silyl Acetals

ChemInform Abstract: Double Nucleophilic Addition to Acrolein with Ketene Silyl Acetals and Allylborolanes Catalyzed by Proline.

ChemInform ◽  
2011 ◽  
Vol 43 (2) ◽  
pp. no-no
Author(s):  
Makoto Shimizu ◽  
Mami Kawanishi ◽  
Akinori Itoh ◽  
Isao Mizota ◽  
Iwao Hachiya
Keyword(s):  
Nucleophilic Addition ◽  
Silyl Acetals

Thiourea-catalyzed nucleophilic addition of TMSCN and ketene silyl acetals to nitrones and aldehydes

2003 ◽  
Vol 44 (14) ◽  
pp. 2817-2821 ◽  
Author(s):  
Tomotaka Okino ◽  
Yasutaka Hoashi ◽  
Yoshiji Takemoto
Keyword(s):  
Nucleophilic Addition ◽  
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.

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