Diastereoselective addition of 2-alkoxy-2-fluoroacetate to N-(tert-butylsulfinyl)imines: Synthesis of α-alkoxy-α-fluoro-β-amino acids

被引：1

作者：

Wei, Jie ^{[1
]}

Ning, Li-Wen ^{[1
]}

Li, Ya ^{[1
]}

机构：

[1] Shanghai Univ Engn Sci, Sch Chem & Chem Engn, 333 Longteng Rd, Shanghai 201620, Peoples R China

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2023年 / 268卷

关键词：

Fluorine; Fluoroalkylation; Amino acid; Addition reaction; Asymmetric synthesis; ASYMMETRIC MANNICH REACTION; ENANTIOSELECTIVE SYNTHESIS; MEDICINAL CHEMISTRY; AMINO ACIDS; FLUORINE; ESTERS; METAL; TRIFLUOROMETHYLATION; CONSTRUCTION; DERIVATIVES;

D O I：

10.1016/j.jfluchem.2023.110118

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A diastereoselective Mannich-type reaction of 2-alkoxy-2-fluoroacetate and N-(tert-butylsulfinyl)imines is reported. This protocol provides a straightforward route to & alpha;-alkoxy-& alpha;-fluoro-& beta;-amino acids in good yields and moderate to high diastereoselectivities. This approach uses readily accessible starting materials and is operationally simple. Additionally, the stereochemistry of the current reaction was different from that of the known addition of comparable nonfluorinated 2-alkoxycarboxylic esters to N-sulfinyl imines. An open transition state (rather than a closed one) is proposed to explain the stereochemical outcome.

引用

页数：10