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

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[4] ONE-STEP BICYCLIZATION BY WAY OF TANDEM TRANSESTERIFICATION, INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION OF ALPHA-METHOXYCARBONYLNITRONES WITH ALLYL ALCOHOLS IN THE PRESENCE OF TITANIUM ISOPROPOXIDE [J].

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[5]

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