Synthesis of Isoxazolines from Nitroalkanes via a [4+1]-Annulation Strategy
A novel access to isoxazolines was developed using the [4+1]-annulation of α-keto-stabilized sulfur ylides with N,N-bis(siloxy)enamines derived from aliphatic nitro compounds. The resulting 5-keto-substituted isoxazolines were shown to be convenient precursors of polysubstituted 3-hydroxypyrrolidines via the one-pot catalytic N?O hydrogenolysis/intramolecular reductive amination sequence. Application of this approach to the formal synthesis of Merck's potent NK1 receptor antagonist was demonstrated. (Figure presented.).
Boron Trifluoride-Assisted Alkylation of 2-Isoxazolines. A novel Route to N-Unsubstituted Isoxazolines
In the presence of boron trifluoride, 2-isoxazolines undergo the addition of organolithiums to afford N-unsubstituted isoxazolines in moderate to good yields.
Uno, Hidemitsu,Terakawa, Tetsuya,Suzuki, Hitomi
p. 1079 - 1082
(2007/10/02)
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