Zinc(II)-Catalyzed Mannich-type Reactions of Hydrazones with Difluoroenoxysilane and Its Application in the Synthesis of Optically Active 2,2-Difluoro-3-oxo-benzohydrazide

被引：42

作者：

Yuan, Zhiliang ^{[1
]}

Wei, Yin ^{[2
]}

Shi, Min ^{[1
,2
]}

机构：

[1] E China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai 200237, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2010年 / 28卷 / 09期

基金：

中国国家自然科学基金;

关键词：

Zn(OTf)(2); Mannich-type reaction; hydrazone; difluoroenoxysilane; asymmetric Mannich-type reaction; chiral phosphine-oxazoline ligand; FORMAL ALPHA-ADDITION; ASYMMETRIC ALLYLATION; ENANTIOSELECTIVE TRIFLUOROMETHYLATION; N-ACYLHYDRAZONES; AMINO; ESTERS; ACID; DERIVATIVES; KETONES; IMINES;

D O I：

10.1002/cjoc.201090289

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

With the catalysis of Zn(OTf)(2), Mannich-type reactions of various aromatic hydrazones 1 with difluoroenoxysilane 2 proceeded smoothly to produce 2,2-difluoro-3-oxo-benzohydrazides in 27%-78% yields in THF or DCM under mild conditions. An unexpected monofluorination of hydrazone 1m with difluoroenoxysilane 2 was also disclosed in this paper. The first example of the asymmetric Mannich-type reaction of hydrazone 1a with difluoroenoxysilane 2 using chiral phosphine-oxazoline ligand has been reported, giving the adduct 3a in good yields and moderate enantioselectivities under mild conditions.

引用

页码：1709 / 1716

页数：8

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