Chiral π-Cu(II) Catalysts for the Enantioselective α-Amination of N-Acyl-3,5-dimethylpyrazoles

被引：3

作者：

Nishimura, Kazuki ^{[1
]}

Ogura, Yoshihiro ^{[1
]}

Takeda, Kazuki ^{[1
]}

Guo, Weiwei ^{[1
]}

Ishihara, Kazuaki ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Nagoya 4648603, Japan

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 41期

关键词：

1,3-DICARBONYL COMPOUNDS; ELECTROPHILIC AMINATION; CATION; KETONES; DESIGN; PROPIOLOYLPYRAZOLES; CYCLOADDITION; CYANOACETATES; DERIVATIVES; COMPLEXES;

D O I：

10.1021/acs.orglett.2c03249

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the highly enantioselective alpha-amination of N- acyl-3,5-dimethylpyrazoles with dialkyl azodicarboxylates, catalyzed by in situ generated pi-Cu(II) complexes that consist of Cu(OTf)2 and N- (5H-dibenzo[a,d][7]annulen-5-yl)-L-alanine-derived amides, to give the corresponding products as D-alpha-amino acid derivatives (up to >99% yield and 99% ee). The site-selectivity and enantioselectivity can be satisfactorily explained by the coordination of dialkyl azodicarboxylate with pi-Cu(II) complex. The synthetic potential of this one-pot transformation to the alpha-amino ester is also described.

引用

页码：7685 / 7689

页数：5

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