MAGNESIUM BROMIDE-PROMOTED E/Z-ISOMERIZATION OF CARBONYL-CONJUGATED NITRONES AND HIGHLY STEREOSELECTIVE AND REGIOSELECTIVE CYCLOADDITIONS TO ALLYLIC ALCOHOL DIPOLAROPHILES
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KANEMASA, S
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KYUSHU UNIV, GRAD SCH ENGN SCI, DEPT MOLEC SCI & TECHNOL, KASUGA, FUKUOKA 816, JAPANKYUSHU UNIV, GRAD SCH ENGN SCI, DEPT MOLEC SCI & TECHNOL, KASUGA, FUKUOKA 816, JAPAN
KANEMASA, S
[1
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TSURUOKA, T
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KYUSHU UNIV, GRAD SCH ENGN SCI, DEPT MOLEC SCI & TECHNOL, KASUGA, FUKUOKA 816, JAPANKYUSHU UNIV, GRAD SCH ENGN SCI, DEPT MOLEC SCI & TECHNOL, KASUGA, FUKUOKA 816, JAPAN
TSURUOKA, T
[1
]
机构:
[1] KYUSHU UNIV, GRAD SCH ENGN SCI, DEPT MOLEC SCI & TECHNOL, KASUGA, FUKUOKA 816, JAPAN
A Lewis acid promotes the E- to Z-isomerization of carbonyl-conjugated nitrones. The MgBr2.Et(2)O-catalyzed cycloadditions to allylic alcohols lead to the exclusive formation of the exo-stereoisomers of isoxazolidine-5-methanols. Participation of the Z-nitrone/MgBr2 complexes is suggested.