A modular olefination reaction between aldehydes and diborylsilylmethide lithium salts

2021 ◽  
Author(s):  
Elena Fernandez ◽  
Oriol Salvado
Keyword(s):  
Wittig Reaction ◽  
Aromatic Aldehydes ◽  
Lithium Salts ◽  
Unsaturated Aldehydes ◽  
Trisubstituted Alkenes

We describe the preparation of densely functionalised 1,1,-silylborylated trisubstituted alkenes, via boron-Wittig reaction, between LiC(Bpin)2(SiMe3) and aliphatic or aromatic aldehydes. The condensation of diborylsilylmethide lithium salts with α,β-unsaturated aldehydes provides...

The Wittig Reaction of 2-t-Butoxycarbonyl-1-methoxycarbonylethylidenetriphenylphosphorane: A Surrogate for the Stobbe Reaction

1987 ◽  
Vol 40 (10) ◽  
pp. 1737 ◽  
Author(s):  
MA Rizzacasa ◽  
MV Sargent
Keyword(s):  
Wittig Reaction ◽  
Aromatic Aldehydes ◽  
High Yield

The reaction of 2-t-butoxycarbonyl-l-methoxycarbonylethylidenetriphenylphosphorane (3) with a range of aromatic aldehydes has been explored. The resultant itaconic esters, obtained in high yield, are readily converted into methyl 4-acetoxynaphthalene-2-carboxylates.

Decarboxylative Umpolung Synthesis of Amines from Carbonyl Compounds

Synlett ◽  
2020 ◽  
Vol 31 (16) ◽  
pp. 1543-1550
Author(s):  
Baoguo Zhao ◽  
Wen-Wen Chen
Keyword(s):  
Carbonyl Compounds ◽  
Aromatic Aldehydes ◽  
High Reactivity ◽  
Mild Conditions ◽  
Intramolecular Reaction ◽  
Unsaturated Aldehydes ◽  
Recent Advances ◽  
Intermolecular Reaction ◽  
Aldehydes And Ketones

2-Azaallyl anions are valuable intermediates which have versatile applications in functionalization with various electrophiles. Decarboxylation of the imines formed from aromatic aldehydes and α,α-diphenylglycine provides an interesting and efficient way to generate delocalized 2-azaallyl anions, which display high reactivity toward different electrophiles with excellent regioselectivity at the diphenylketimino aryl carbon of the 2-azaallyl anions. The transformation produces various amines in good yields under very mild conditions. This Synpacts article highlights the recent advances on the decarboxylative umpolung synthesis of amines from carbonyl compounds.1 Introduction2 Decarboxylative Umpolung Reactions of Carbonyl Compounds with Different Electrophiles2.1 Reaction with π-Allyl–Pd(II) Species2.2 Reaction with Morita–Baylis–Hillman Adducts2.3 Reaction with Imines2.3.1 Intermolecular Reaction with N-Ts Imines2.3.2 Intramolecular Reaction with Chiral N-tert-Butanesulfinyl Imines2.4 Reaction with Aldehydes and Ketones3 Decarboxylative Umpolung Reaction of α,β-Unsaturated Aldehydes with Aldehydes4 Conclusion

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