Asymmetric α-Azidation Reaction of β-Ketoesters Catalyzed by Chiral Tin Alkoxides

被引：4

作者：

Yanagisawa, Akira ^{[1
]}

Takagi, Kotaro ^{[1
]}

Horiguchi, Moe ^{[1
]}

Dezaki, Kohei ^{[1
]}

Marui, Tomoki ^{[1
]}

Saito, Etsushi ^{[1
]}

Ebihara, Toru ^{[2
]}

Russell, Go M. ^{[2
]}

Watanabe, Takamichi ^{[3
]}

Midorikawa, Koji ^{[3
]}

机构：

[1] Chiba Univ Inage, Mol Chiral Res Ctr, Grad Sch Sci, Dept Chem, Chiba 2638522, Japan

[2] Chiba Univ Inage, Fac Sci, Dept Chem, Chiba 2638522, Japan

[3] Nippoh Chem Co Ltd, 1240 Matsumaru, Isumi, Chiba 2980104, Japan

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 12卷 / 08期

关键词：

asymmetric catalysis; azidation; beta-ketoester; hypervalent iodine reagent; tin catalyst; KETO-ESTERS; ANALOGS;

D O I：

10.1002/ajoc.202300213

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic enantioselective alpha-azidation reaction of beta-ketoesters with an azidated hypervalent iodine reagent was achieved by using an (R)-BINOL-derived chiral tin dibromide possessing 4-t-butylphenyl groups at the 3- and 3'-positions as the chiral precatalyst in the presence of sodium ethoxide and ethanol. Optically active alpha-azido-beta-ketoesters having a chiral tertiary carbon were obtained in moderate to high yields under the influence of the chiral tin diethoxide generated in situ.

引用

页数：4

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