MiPNO, a new chiral cyclic nitrone for enantioselective amino acid synthesis the cycloaddition approach

被引：23

作者：

Thiverny, Maryse ^{[1
]}

Philouze, Christian ^{[1
]}

Chavant, Pierre Yves ^{[1
]}

Blandin, Veronique ^{[1
]}

机构：

[1] Univ Grenoble 1, CNRS, ICMG FR 2607, Dept Chim Mol,UMR 5250, F-38041 Grenoble, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 04期

关键词：

1,3-DIPOLAR CYCLOADDITION; ALPHA-ALKOXYCARBONYLNITRONES; BUILDING-BLOCKS; N-HYDROXY; ACCESS; REARRANGEMENT; PRECURSORS; PRINCIPLE; PEPTIDES; REAGENTS;

D O I：

10.1039/b918612c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The resolution of chiral nitrones via derivatization of hydroxylamines was applied to MiPNO, a new, stable, easily prepared chiral cyclic nitrone. The application of MiPNO in totally regio- and diastereo-selective 1,3-dipolar cycloaddition reactions provides an expeditious enantioselective access to unusual gamma-hydroxy alpha-amino acids.

引用

页码：864 / 872

页数：9

共 50 条

[1] Enantioselective synthesis of cyclic quaternary α-amino acid derivatives by chiral phosphoric acid catalysis
Wang, Lei
Rahman, Abdul
Lin, Xufeng
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (28) : 6033 - 6041
[2] Asymmetric [3+2] cycloaddition reaction of a chiral cyclic nitrone for the synthesis of new tropane alkaloids
Esteban, Alberto
Izquierdo, Ignacio
Garcia, Nieves
Sexmero, Maria J.
Garrido, Narciso M.
Marcos, Isidro S.
Sanz, Francisca
Jambrina, Pablo G.
Ortega, Pablo
Diez, David
TETRAHEDRON, 2020, 76 (0I)
[3] A Nitrone Dipolar Cycloaddition Strategy toward an Enantioselective Synthesis of Massadine
Cannon, Jeffrey S.
ORGANIC LETTERS, 2018, 20 (13) : 3883 - 3887
[4] DIASTEREOCONTROLLED AND ENANTIOCONTROLLED SYNTHESIS OF (-)-ALLOSEDAMINE VIA CYCLOADDITION OF A CHIRAL NITRONE
OPPOLZER, W
DEERBERG, J
TAMURA, O
HELVETICA CHIMICA ACTA, 1994, 77 (02) : 554 - 560
[5] Synthesis of a new chiral cyclic β-amino alcohol
Shen, ZX
Liang, J
Zhang, YW
CHINESE CHEMICAL LETTERS, 2000, 11 (01) : 9 - 10
[6] Synthesis of a New Chiral Cyclicβ-Amino Alcohol
Zong Xuan SHEN
Jing LIANG
Ya Wen ZHANG(School of Chemistry and Chemical Engineering
ChineseChemicalLetters, 2000, (01) : 9 - 10
[7] TOWARD THE SYNTHESIS OF (-)-CODEINE BY CHIRAL AUXILIARY -MEDIATED NITRONE CYCLOADDITION
Rautschek, Julia
Metz, Peter
HETEROCYCLES, 2017, 95 (02) : 1106 - 1120
[8] Stereocontrolled synthesis of multi-functionalized β-substituted α-amino acids:: Nitrone cycloaddition approach
Tamura, O
Yoshida, S
Sugita, H
Mita, N
Uyama, Y
Morita, N
Ishiguro, M
Kawasaki, T
Ishibashi, H
Sakamoto, M
SYNLETT, 2000, (11) : 1553 - 1556
[9] Preparation and evaluation of a cyclic acyl nitrone as a synthon for stereospecific α-amino acid synthesis
Baldwin, SW
Young, BG
McPhail, AT
TETRAHEDRON LETTERS, 1998, 39 (38) : 6819 - 6822
[10] A new chiral catalyst for the enantioselective Strecker synthesis of α-amino acids
Huang, JK
Corey, EJ
ORGANIC LETTERS, 2004, 6 (26) : 5027 - 5029

← 1 2 3 4 5 →