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Efficient synthesis of 4-(3 '-furanyl)butenolide derivatives via Pd-II-catalyzed oxidative heterodimeric cyclization reaction of 2,3-allenoic acids and 1,2-allenyl ketones
其他题名二价鈀催化2,3-联烯酸与1,2-联烯酮的双分子关联反应
Ma SM(麻生明); Yu ZQ(俞瞻前)
2004
发表期刊Chem.-Eur. J.
ISSN0947-6539
卷号10期号:8页码:2078-2087
摘要The oxidative cyclization/dimerization reaction between two classes of allenes with different functionalities was reported to provide an efficient route to polysubstituted 4-(3'-furanyl)-2(5H)-furanones, which are not readily available from the known methods. The highly optically active butenolides could be easily formed from the optically active 2,3-allenoic acids, which was obtained conveniently through chiral resolution with optically active amines, that is, cinchonidine or a-methyl benzylamine. A mechanistic study showed that the reaction proceeded via a matched double oxypalladation-reductive elimination process. The Pd-II species may be regenerated via the subsequent cyclometallation of two equivalents of 1,2-allenyl ketones with Pd-0 and protonlysis of Pd enolates formed with the in situ generated HCI.
学科领域金属有机化学
部门归属中国科学院上海有机化学研究所有机金属化学实验室
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收录类别SCI
语种英语
WOS记录号WOS:000221025200024
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文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/11976
专题金属有机化学国家重点实验室
通讯作者Ma SM(麻生明)
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GB/T 7714
Ma SM,Yu ZQ. Efficient synthesis of 4-(3 '-furanyl)butenolide derivatives via Pd-II-catalyzed oxidative heterodimeric cyclization reaction of 2,3-allenoic acids and 1,2-allenyl ketones[J]. Chem.-Eur. J.,2004,10(8):2078-2087.
APA 麻生明,&俞瞻前.(2004).Efficient synthesis of 4-(3 '-furanyl)butenolide derivatives via Pd-II-catalyzed oxidative heterodimeric cyclization reaction of 2,3-allenoic acids and 1,2-allenyl ketones.Chem.-Eur. J.,10(8),2078-2087.
MLA 麻生明,et al."Efficient synthesis of 4-(3 '-furanyl)butenolide derivatives via Pd-II-catalyzed oxidative heterodimeric cyclization reaction of 2,3-allenoic acids and 1,2-allenyl ketones".Chem.-Eur. J. 10.8(2004):2078-2087.
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