Role of a Protected Vicinal Diol Controller in Intramolecular [3 + 2] Cycloaddition Reactions of Chiral Acyclic Alkenyl Nitrones: Syntheses of Enantiomerically Pure Tetrasubstituted Cyclobutylamines

1994 ◽  
Vol 59 (16) ◽  
pp. 4375-4377 ◽  
Author(s):  
Seiki Saito ◽  
Teruhiko Ishikawa ◽  
Toshio Moriwake
Keyword(s):  
Cycloaddition Reactions ◽  
Enantiomerically Pure ◽  
Vicinal Diol

Role of Vicinal Diol Controller in Discriminating π(C=C)-Faces of Dipolarophile in Nitrone-Olefin Cycloaddition Reactions

Synlett ◽  
1994 ◽  
Vol 1994 (04) ◽  
pp. 279-281 ◽  
Author(s):  
Seiki Saito ◽  
Teruhiko Ishikawa ◽  
Toshio Moriwake
Keyword(s):  
Cycloaddition Reactions ◽  
Vicinal Diol

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.

A mechanistic MEDT study of the competitive catalysed [4+2] and [2+2] cycloaddition reactions between 1-methyl-1-phenylallene and methyl acrylate: the role of Lewis acid on the mechanism and selectivity

2018 ◽  
Vol 29 (6) ◽  
pp. 1709-1721 ◽  
Author(s):  
Leila Barama ◽  
Brahim Bayoud ◽  
Fouad Chafaa ◽  
Abdelmalek Khorief Nacereddine ◽  
Abdelhafid Djerourou
Keyword(s):  
Lewis Acid ◽  
Methyl Acrylate ◽  
Cycloaddition Reactions
Sign in / Sign up

Export Citation Format

Share Document