Attempted Asymmetric Syntheses Involving the Grignard Reagent in Optically Active Solvents

1942 ◽  
Vol 64 (12) ◽  
pp. 2842-2844 ◽  
Author(s):  
D. S. Tarbell ◽  
Mark C. Paulson
Keyword(s):  
Grignard Reagent ◽  
Optically Active ◽  
Asymmetric Syntheses

ChemInform Abstract: Synthesis of Optically Active α-Furfuryl Amine Derivatives and Application to the Asymmetric Syntheses

ChemInform ◽  
2010 ◽  
Vol 30 (51) ◽  
pp. no-no
Author(s):  
Wei-Shan Zhou ◽  
Zhi-Hui Lu ◽  
Yi-Ming Xu ◽  
Li-Xin Liao ◽  
Zhi-Min Wang
Keyword(s):  
Optically Active ◽  
Asymmetric Syntheses

Use of Menthyl 2-Methoxynaphthalene-1-sulfinates in the Andersen Synthesis of Optically Active Sulfoxides. Facile Cleavage by Grignard Reagents of Some Aromatic Methyl Ethers

1994 ◽  
Vol 47 (10) ◽  
pp. 1925 ◽  
Author(s):  
KH Bell ◽  
LF Mccaffery
Keyword(s):  
Grignard Reagent ◽  
Methoxy Group ◽  
Optically Active ◽  
Grignard Reagents ◽  
Sulfinyl Group

The pure crystalline diastereomers (1R,2S,5R)-menthyl (R)- and (S)-2-methoxynaphthalene-1-sulfinate (1b) have been prepared and, by reaction with Grignard reagents (the Andersen procedure), converted into optically active alkyl and aryl 2-methoxynaphthyl sulfoxides in 67-77% yields. Use of an excess of Grignard reagent results in facile O-alkyl cleavage of the methoxy group to the corresponding naphthol or a competing loss of the alkyl- or aryl- sulfinyl group to form 2-methoxynaphthalene. Pure diastereomers of menthyl 2,7- dimethoxynaphthalene-1-sulfinate (2b) and menthyl 4-methoxynaphthalene-1-sulfinate (3b) have also been prepared and their reactions with Grignard reagents have been studied.

Asymmetric syntheses with a new optically active perhydronaphthalene based chiral auxiliary

Tetrahedron ◽  
1993 ◽  
Vol 49 (42) ◽  
pp. 9593-9604 ◽  
Author(s):  
David P.G. Hamon ◽  
Jeffrey W. Holman ◽  
Ralph A. Massy-Westropp
Keyword(s):  
Optically Active ◽  
Chiral Auxiliary ◽  
Asymmetric Syntheses
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