Synthesis of α-amino phosphonates by diastereoselective addition of diethyl phosphite sodium salt to aldimines derived from Betti base

被引:5
|
作者
Nikitina, Kristina A. [1 ]
Metlushka, Kirill E. [1 ,2 ]
Sadkova, Dilyara N. [1 ]
Shaimardanova, Liliya N. [1 ]
Alfonsov, Vladimir A. [1 ]
机构
[1] Russian Acad Sci, Kazan Sci Ctr, AE Arbuzov Inst Organ & Phys Chem, Kazan 420088, Russia
[2] Kazan Volga Reg Fed Univ, AM Butlerov Inst Chem, Kazan 420008, Russia
基金
俄罗斯基础研究基金会;
关键词
RING-CHAIN TAUTOMERISM; AMINOPHOSPHONIC ACIDS; STEREOSELECTIVE-SYNTHESIS; DERIVATIVES;
D O I
10.1016/j.mencom.2016.09.009
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A diastereoselective (de 80-92%) synthesis of alpha-amino phosphonates was accomplished by reaction of diethyl phosphite sodium salt with 3-R-1-pheny1-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines being the products of aminoacetalization of aldehydes with 1-(alpha-aminobenzyl)-2-naphthol (Betti base).
引用
收藏
页码:395 / 396
页数:2
相关论文
共 50 条
  • [1] A new and expedient diastereoselective synthesis of α-(hydroxyamino)phosphonates and α-aminophosphonates by silyl triflate promoted diethyl phosphite addition to chiral N-benzyl nitrones
    De Risi, C
    Perrone, D
    Dondoni, A
    Pollini, GP
    Bertolasi, V
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (10) : 1904 - 1914
  • [2] Efficient palladium-catalyzed synthesis of aminopyridyl phosphonates from bromopyridines and diethyl phosphite
    Bessmertnykh, Alla
    Douaihy, Christiane Morkos
    Muniappan, Sankar
    Guilard, Roger
    [J]. SYNTHESIS-STUTTGART, 2008, (10): : 1575 - 1579
  • [3] ASYMMETRIC-SYNTHESIS OF ALPHA-AMINOPHOSPHONATES VIA DIASTEREOSELECTIVE ADDITION OF LITHIUM DIETHYL PHOSPHITE TO CHELATING IMINES
    YAGER, KM
    TAYLOR, CM
    SMITH, AB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) : 9377 - 9378
  • [4] Synthesis of chiral ligands derived from the Betti base and their use in the enantioselective addition of diethylzinc to aromatic aldehydes
    Lu, J
    Xu, XN
    Wang, C
    He, HG
    Hu, YF
    Hu, HW
    [J]. TETRAHEDRON LETTERS, 2002, 43 (46) : 8367 - 8369
  • [5] Asymmetric synthesis of alpha-amino phosphonic acids by diastereoselective addition of trimethyl phosphite onto chiral oxazolidines
    Maury, C
    Gharbaoui, T
    Royer, J
    Husson, HP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11): : 3687 - 3693
  • [6] ASYMMETRIC-SYNTHESIS OF DIETHYL ALPHA-AMINO-ALPHA-ALKYL-PHOSPHONATES BY ALKYLATION OF THE CHIRAL SCHIFF-BASE DERIVED FROM (+)-KETOPINIC ACID AND DIETHYLAMINOMETHYL PHOSPHONATE
    FERRARI, M
    JOMMI, G
    MIGLIERINI, G
    PAGLIARIN, R
    SISTI, M
    [J]. SYNTHETIC COMMUNICATIONS, 1992, 22 (01) : 107 - 123
  • [7] Catalyst- and Solvent-Free Synthesis of α-Amino Polyfluoroalkylphosphonates from Bis(fluoroalkyl) Phosphonates and Aldimines
    Arbuzova, Svetlana N.
    Gusarova, Nina K.
    Kazantseva, Tatyana I.
    Verkhoturova, Svetlana I.
    Zinchenko, Sergey V.
    Kolyvanov, Nikita A.
    Trofimov, Boris A.
    [J]. SYNTHESIS-STUTTGART, 2020, 52 (10): : 1531 - 1540
  • [8] Diastereoselective conjugate addition to (+)-camphorsulfonic acid derived nitroalkenes:: Synthesis of α-hydroxy and α-amino acids
    Barrett, AGM
    Braddock, DC
    Christian, PWN
    Pilipauskas, D
    White, AJP
    Williams, DJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17): : 5818 - 5823
  • [9] Rh-Catalyzed diastereoselective addition of arylboronic acids to α-keto N-tert-butanesulfinyl aldimines: synthesis of α-amino ketones
    Wang, Cece
    Zhou, Lu
    Qiu, Jian
    Yang, Kai
    Song, Qiuling
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (04): : 1016 - 1022
  • [10] Direct Synthesis of Amino-substituted Aromatic Phosphonates via Palladium-catalyzed Coupling of Aromatic Mono- and Dibromides with Diethyl Phosphite
    Bessmertnykh, Alla
    Douaihy, Christiane Morkos
    Guilard, Roger
    [J]. CHEMISTRY LETTERS, 2009, 38 (07) : 738 - 739