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

共 50 条

[21] The enantiospecific synthesis of functionalised pipecolic acids as constrained analogues of lysine
Murray, PJ
Starkey, ID
TETRAHEDRON LETTERS, 1996, 37 (11) : 1875 - 1878
[22] YComputational studies of the conformational preferences of fluorinated amino acids.
Gann, JL
Urban, JJ
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U498 - U498
[23] Flow Synthesis of Fluorinated α-Amino Acids
Vukelic, Stella
Ushakov, Dmitry B.
Gilmore, Kerry
Koksch, Beate
Seeberger, Peter H.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (14) : 3036 - 3039
[24] A NOVEL SYNTHESIS OF FLUORINATED PHOSPHONOACETIC ACIDS
BLACKBURN, GM
BROWN, D
MARTIN, SJ
JOURNAL OF CHEMICAL RESEARCH-S, 1985, (03): : 92 - 93
[25] Asymmetric synthesis of fluorinated amino acids
Kumar, JSD
Katagiri, T
Uneyama, K
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U820 - U820
[26] CONFORMATIONAL-ANALYSIS OF FLUORINATED COPOLYMERS OF TETRAFLUOROETHYLENE
VILLANI, V
PUCCIARIELLO, R
FUSCO, R
COLLOID AND POLYMER SCIENCE, 1991, 269 (05) : 477 - 482
[27] Enantioselective synthesis of 2-substituted pipecolic acids and its application
Hou, DR
Hung, SY
Hu, CC
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U2598 - U2599
[28] Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids
Marjanovic, Jasna
Ferjancic, Zorana
Saicic, Radomir N.
TETRAHEDRON, 2015, 71 (38) : 6784 - 6789
[29] Diastereoselective synthesis and conformational analysis of 4,5-difluoropipecolic acids
Chen, Suo
Ruan, Yao
Lu, Ji-Liang
Hunter, Luke
Hu, Xiang-Guo
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (40) : 8192 - 8198
[30] Recent Advances in the Synthesis of Fluorinated Amino Acids
Qiu, Xiao-Long
Qing, Feng-Ling
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (18) : 3261 - 3278

← 1 2 3 4 5 →