Tetrahedron Letters p. 5019 - 5022 (1995)
Update date:2022-08-04
Topics:
Kanemasa, Shuji
Tsuruoka, Takashi
Yamamoto, Hidetoshi
Magnesium and zinc ion-mediated cycloaddition reactions of a carbonyl-conjugated nitrone, (Z)-N-(benzoylmethylene)aniline N-oxide to the allylic alcohols bearing a chirality at α-position give isoxazolidine-5-alcohol and isoxazolidine-4-alcohol derivatives, respectively, both in highly lk-1,2-inductive manners. α,α-Disubstitution of allylic alcohol dipolarophiles virtually inhibits the zinc ion-catalyzed reaction paths, and use of a coordinating solvent in the magnesium ion-catalyzed reactions leads to the reversal of regioselectivity.Reaction mechanism for the metal ion-catalyzed competitive cycloadditions is proposed. - Keywords: nitrone cycloaddition; allylic alcohol; diastereofacial selectivity; rate acceleration; regiocontrol
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