Synthesis of enantiomeric β-amino ketones via 1,3-dipolar cycloaddition and chromatographic resolution

1994 ◽  
Vol 72 (5) ◽  
pp. 1347-1350 ◽  
Author(s):  
Chantal Louis ◽  
Sibel Mill ◽  
Vincent Mancuso ◽  
Claude Hootelé
Keyword(s):  
Column Chromatography ◽  
Asymmetric Induction ◽  
High Yield ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Chromatographic Resolution

The cycloaddition reactions of 3,4,5,6-tetrahydropyridine 1-oxide 1 with the homochiral alkynyl sulfoxides 6a–e proceed in high yield to afford, with low asymmetric induction, mixtures of diastereomeric isoxazolines that are readily separated by column chromatography. The resolved isoxazolines can be subsequently converted, by hydrogenolysis, to enantiomeric β-amino ketones.

Multicomponent 1,3-Dipolar Cycloaddition Reactions in the Construction of Hybrid Spiroheterocycles

2013 ◽  
Vol 17 (18) ◽  
pp. 1929-1956 ◽  
Author(s):  
Natarajan Arumugam ◽  
Raju Kumar ◽  
Abdulrahman Almansour ◽  
Subbu Perumal
Keyword(s):  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions

π-Facial Selectivity in 1,3-Dipolar Cycloaddition Reactions of α-Methylidene-γ-lactone Substituted by 4-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl Group in γ-Position

2002 ◽  
Vol 67 (3) ◽  
pp. 353-364 ◽  
Author(s):  
Petr Melša ◽  
Ctibor Mazal
Keyword(s):  
Double Bond ◽  
Carboxylic Acid ◽  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Enantiomerically Pure ◽  
Nitrile Imine ◽  
Facial Selectivity ◽  
Excellent Selectivity

Diastereoselectivity of 1,3-dipolar cycloaddition reactions of benzyl azide, diazomethane, a nitrile oxide and a nitrile imine to α-methylidene-γ-lactone dipolarophile was effectively controlled by a bulky γ-substituent, 4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl in γ-position of the dipolarophile. The dipoles added from the less hindered face of the double bond with an excellent selectivity. Enantiomerically pure dipolarophile was prepared from the easily available (S)-5-oxotetrahydrohydrofuran-2-carboxylic acid.

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