Dynamic Kinetic Resolution of Azlactones by a Chiral N,N-Dimethyl-4-aminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Importance of Amide Groups

被引：28

作者：

Mandai, Hiroki ^{[1
]}

Hongo, Kohei ^{[1
]}

Fujiwara, Takuma ^{[1
]}

Fujii, Kazuki ^{[1
]}

Mitsudo, Koichi ^{[1
]}

Suga, Seiji ^{[1
]}

机构：

[1] Okayama Univ, Grad Sch Nat Sci & Technol, Div Appl Chem, Kita Ku, 3-1-1 Tsushima Naka, Okayama 7008530, Japan

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 16期

关键词：

ACYL TRANSFER CATALYSIS; DESYMMETRIZATION;

D O I：

10.1021/acs.orglett.8b01960

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A dynamic kinetic resolution (DKR) of azlactones in the presence of benzoic acid and a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1i having two amide groups at the 3,3'-positions of a binaphthyl unit is developed. The reaction proceeded smoothly with a wide range of azlactones to provide alpha-amino acid derivatives with good to high enantiomeric ratios (er's). A multigram-scale reaction (2.5 g) for the DKR of azlactone 2d was also demonstrated, and the resulting product was converted to unnatural alpha-amino acid 6d'.

引用

收藏

页码：4811 / 4814

页数：4

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