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

被引：55

作者：

KANEMASA, S ^{[1
]}

TSURUOKA, T ^{[1
]}

YAMAMOTO, H ^{[1
]}

机构：

[1] KYUSHU UNIV, INTERDISCIPLINARY GRAD SCH ENGN SCI, DEPT MOLEC SCI & TECHNOL, KASUGA, FUKUOKA 816, JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 28期

关键词：

NITRONE CYCLOADDITION; ALLYLIC ALCOHOL; DIASTEREOFACIAL SELECTIVITY; RATE ACCELERATION; REGIOCONTROL;

D O I：

10.1016/0040-4039(95)00911-U

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 alpha-position give isoxazolidine-5-alcohol and isoxazolidine-4-alcohol derivatives, respectively, both in highly lk-1,2-inductive manners. alpha,alpha-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.

引用

页码：5019 / 5022

页数：4

共 5 条

[1] Metal ion-mediated diastereoface-selective 1,3-dipolar cycloaddition of nitrile oxides with dipolarophiles bearing an oxazolidinone chiral auxiliary
Yamamoto, H
Watanabe, S
Kadotani, K
Hasegawa, M
Noguchi, M
Kanemasa, S
TETRAHEDRON LETTERS, 2000, 41 (17) : 3131 - 3136
[2] Direct oxidation of Δ2-isoxazolines synthesis by metal ion-mediated diastereoface-selective 1,3-dipolar cycloaddition with "activated'' DMSO
Ben Hamadi, Naoufel
Msaddek, Moncef
ARABIAN JOURNAL OF CHEMISTRY, 2017, 10 : S800 - S803
[3] Direct oxidation of Δ2-isoxazolines synthesis by metal ion-mediated diastereoface-selective 1,3-dipolar cycloaddition with "activated" DMSO (vol 10, pg S800, 2017)
Ben Hamadi, Naoufel
Msaddek, Moncef
ARABIAN JOURNAL OF CHEMISTRY, 2019, 12 (03) : 447 - 447
[4] Catalytic Efficiency, Ligand Acceleration, and Concentration Effect in Magnesium Ion Mediated 1,3-Dipolar Cycloadditions of Mesitonitrile Oxide to Allylic Alcohols
Kanemasa, S.
Okuda, K.
Yamamoto, H.
Kaga, S.
Tetrahedron Letters, 38 (23):
[5] Catalytic efficiency, ligand acceleration, and concentration effect in magnesium ion mediated 1,3-dipolar cycloadditions of mesitonitrile oxide to allylic alcohols
Kanemasa, S
Okuda, K
Yamamoto, H
Kaga, S
TETRAHEDRON LETTERS, 1997, 38 (23) : 4095 - 4098

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