scholarly journals Water opens the door to organolithiums and Grignard reagents: exploring and comparing the reactivity of highly polar organometallic compounds in unconventional reaction media towards the synthesis of tetrahydrofurans

2016 ◽  
Vol 7 (2) ◽  
pp. 1192-1199 ◽  
Author(s):  
Luciana Cicco ◽  
Stefania Sblendorio ◽  
Rosmara Mansueto ◽  
Filippo M. Perna ◽  
Antonio Salomone ◽  
...  
Keyword(s):  
Organometallic Compounds ◽  
Grignard Reagents ◽  
Nucleophilic Additions ◽  
Organolithium Reagents ◽  
Reaction Media

Grignard and organolithium reagents undergo smooth nucleophilic additions to γ-chloroketones “on water”.

Recent Advances in the Synthesis of Enantiomerically Enriched Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols through Addition of Organometallic Reagents to Carbonyl Compounds

Synthesis ◽  
2020 ◽  
Vol 52 (13) ◽  
pp. 1855-1873
Author(s):  
Senthil Narayanaperumal ◽  
Ricardo S. Schwab ◽  
Wystan K. O. Teixeira ◽  
Danilo Yano de Albuquerque
Keyword(s):  
Carbonyl Compounds ◽  
Building Blocks ◽  
Short Review ◽  
Biological Properties ◽  
Enantioselective Synthesis ◽  
Grignard Reagents ◽  
Organometallic Reagents ◽  
Important Family ◽  
Organolithium Reagents ◽  
Organozinc Reagents

Enantiomerically enriched diaryl, aryl heteroaryl, and dihetero­aryl alcohols are an important family of compounds known for their biological properties. Moreover, these molecules are highly privileged scaffolds used as building blocks for the synthesis of pharmaceutically relevant products. This short review provides background on the enantioselective arylation and heteroarylation of carbonyl compounds, as well as, the most significant improvements in this field with special emphasis on the application of organometallic reagents.1 Introduction2 Background on the Enantioselective Synthesis of Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols3 Organozinc Reagents4 Organolithium Reagents5 Grignard Reagents6 Organoaluminum Reagents7 Organotitanium Reagents8 Organobismuth Reagents9 Miscellaneous10 Conclusion

Relative reactivities of organometallic compounds. XI Grignard reagents

2010 ◽  
Vol 55 (7) ◽  
pp. 577-585 ◽  
Author(s):  
Henry Gilman ◽  
Edith L. St. John ◽  
Nina B. St. John ◽  
Myrl Lichtenwalter
Keyword(s):  
Organometallic Compounds ◽  
Grignard Reagents

Unprecedented Nucleophilic Additions of Highly Polar Organometallic Compounds to Imines and Nitriles Using Water as a Non-Innocent Reaction Medium

2017 ◽  
Vol 56 (34) ◽  
pp. 10200-10203 ◽  
Author(s):  
Giuseppe Dilauro ◽  
Marzia Dell'Aera ◽  
Paola Vitale ◽  
Vito Capriati ◽  
Filippo Maria Perna
Keyword(s):  
Reaction Medium ◽  
Organometallic Compounds ◽  
Nucleophilic Additions

Reactions of Norbornen-7-one with Organolithium Reagents

1971 ◽  
Vol 49 (13) ◽  
pp. 2223-2228 ◽  
Author(s):  
F. R. S. Clark ◽  
J. Warkentin
Keyword(s):  
Solvent Effects ◽  
Grignard Reagents ◽  
Organolithium Reagents

Alkyllithium reagents (RLi: R = methyl, n-butyl, t-butyl) add to norbornen-7-one either without stereochemical preference (R = n-butyl) or with syn attack favored. This addition selectivity is qualitatively the same as that shown by corresponding alkylmagnesium reagents but competition from reduction is much less important in the case of alkyllithium reagents.Phenyllithium and vinyllithium add preferentially from the anti face, although the corresponding Grignard reagents add selectively from the syn face. Possible causes of the stereoselectivities are considered. Solvent effects on the stereochemistry of addition are small.

Unprecedented Nucleophilic Additions of Highly Polar Organometallic Compounds to Imines and Nitriles Using Water as a Non-Innocent Reaction Medium

2017 ◽  
Vol 129 (34) ◽  
pp. 10334-10337 ◽  
Author(s):  
Giuseppe Dilauro ◽  
Marzia Dell'Aera ◽  
Paola Vitale ◽  
Vito Capriati ◽  
Filippo Maria Perna
Keyword(s):  
Reaction Medium ◽  
Organometallic Compounds ◽  
Nucleophilic Additions

1,2-Nucleophilic additions of organolithium reagents to chiral oxime ethers

1993 ◽  
Vol 71 (6) ◽  
pp. 814-823 ◽  
Author(s):  
R. Karl Dieter ◽  
Ravindra Datar
Keyword(s):  
Nucleophilic Addition ◽  
Chiral Amines ◽  
Addition Reactions ◽  
Nucleophilic Additions ◽  
Organolithium Reagents ◽  
Diastereomeric Excess

Chiral oxime ethers are readily prepared from chiral alkoxyamines derived from ephedrine and norephedrine. These chiral oxime ethers of isobutyraldehyde and benzaldehyde undergo 1,2-nucleophilic addition reactions with alkyllithium reagents (n-BuLi, PhLi and n-BuLi, tert-butyllithium, respectively) to afford the chiral alkoxyamines with a diastereomeric excess of 64–88%. Reduction of the alkoxyamines with LiAlH4 gave the corresponding chiral amines. The diastereoselectivity of the reaction appears to directly mirror the E:Z ratio of the starting oxime ethers.

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