Synthesis and Conformational Analysis of Fluorinated Pipecolic Acids

被引：14

作者：

Singh, Sukhdev ^{[1
,2
]}

Martinez, Claire-Marie ^{[1
]}

Calvet-Vitale, Sandrine ^{[1
]}

Prasad, Ashok K. ^{[2
]}

Prange, Thierry ^{[3
]}

Dalko, Peter I. ^{[1
]}

Dhimane, Hamid ^{[1
]}

机构：

[1] Univ Paris 05, CNRS, UFR Biomed, Lab Chim & Biochim Pharmacol & Toxicol,UMR 8601, F-75270 Paris 06, France

[2] Univ Delhi, Dept Chem, Bioorgan Lab, Delhi 110007, India

[3] Univ Paris 05, CNRS, Fac Pharm 4, Lab Cristallog & RMN Biol,UMR 8015, F-75270 Paris 06, France

来源：

SYNLETT | 2012年 / 16期

关键词：

pipecolic acid; enecarbamate; electrophilic addition; fluorine; stereoselectivity; fluoropipecolate; conformational analysis; PROTEIN DESIGN; AMINO-ACIDS; 3-FLUOROPIPERIDINES; SELECTFLUOR; STABILITY; BOND; TOOL; BOC;

D O I：

10.1055/s-0032-1316770

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short sequence to methyl cis- and trans-5-fluoro pipecolate is described via electrophilic fluorination of a pipecolate-based endocyclic enecarbamate by using Selectfluor (R) as a fluorinating agent. Methyl 5,5-difluoro pipecolate was also obtained by difluorodeoxygenation of the corresponding ketone, which was obtained in two steps from the same enecarbamate. The conformational profile of both methyl 5-fluoropipecolate isomers was investigated by NMR spectroscopy in solution and X-ray crystallography of the corresponding piperidinium picrates.

引用

页码：2421 / 2425

页数：5

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