101161-31-3Relevant academic research and scientific papers
Metal Ion-Mediated Diastereoface-Selective Nitrone Cycloadditions. Reaction Mechanism for the Reversal of Regioselectivity Observed in the Magnesium and Zinc Ion-Mediated Nitrone Cycloadditions of Allylic Alcohols
Kanemasa, Shuji,Tsuruoka, Takashi,Yamamoto, Hidetoshi
, p. 5019 - 5022 (1995)
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
THE REGIOSELECTIVE EFFECT OF THE ALLYLIC SILICON OR OXYGEN ATOM IN 1,3-DIPOLAR CYCLOADDITION OF NITRONES
Niwayama, Satomi,Dan, Shigeyuki,Inouye, Yoshinobu,Kakisawa, Hiroshi
, p. 957 - 960 (2007/10/02)
1,3-Dipolar cycloaddition of nitrones on several allyl silanes, allyl ethers, and allyl alcohol was investigated.The silicon atom in dipolarophiles controlled the regioselectivity in favor for 5-(silylmethyl)isoxazolidines, while the oxygen atom for 4-(al
