Rh(II)-catalyzed intramolecular N-H insertion of D-glucose-derived δ-amino α-diazo β-ketoester:: Synthesis of pyrrolidine iminosugars

被引：18
|
作者：
Vyavahare, Vinod P.
Chattopadhyay, Subrata
Puranik, Vedavati G.
Dhavale, Dilip D. [1 ]
机构：
[1] Univ Pune, Dept Chem, Garware Res Ctr, Pune 411007, Maharashtra, India
[2] Bhabha Atom Res Ctr, Bioorgan Div, Bombay 400085, Maharashtra, India
[3] Natl Chem Lab, Ctr Mat Characterizat, Pune 411008, Maharashtra, India
来源：
SYNLETT | 2007年 / 04期
关键词：
alkaloids; azasugars; carbohydrates; pyrrolidines; rhodium carbenoid; N-H insertion;
D O I：
10.1055/s-2007-970743
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The rhodium acetate catalyzed reaction of D-glucose-derived delta-amino alpha-diazo beta-ketoester allows a stereoselective beta-facial intramolecular N-H insertion reaction that leads to formation of the bicyclic pyrrolidinone ring skeleton in high yield. The sugar-substituted pyrrolidinone thus obtained was elaborated to allow the synthesis of promising glycosidase inhibitors, namely, 2,5-dideoxy2,5-imino-L-glycero-alpha-D-galactoheptitol and 2,5-dideoxy-2,5-imino-D-galactitol.
引用
收藏
页码：559 / 562
页数：4
相关论文
共 42 条
  • [1] Convenient synthesis of polyfunctionalized β-fluoropyrroles from rhodium(II)-catalyzed intramolecular N-H insertion reactions
    Wang, YL
    Zhu, SZ
    ORGANIC LETTERS, 2003, 5 (05) : 745 - 748
  • [2] Rh(II)-catalyzed intramolecular C-H insertion of diazo substrates in water: Scope and limitations
    Candeias, Nuno R.
    Gois, Pedro M. P.
    Afonso, Carlos A. M.
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (15): : 5489 - 5497
  • [3] Facile N-Modification of NH-Tetrazoles via Rh(II)-Catalyzed N-H Insertion Involving Structurally Diverse Diazo Reagents
    Radiupov, Valentin
    Kantin, Grigory
    Dar'in, Dmitry
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 28 (04)
  • [4] ELECTRONIC AMPLIFICATION OF SELECTIVITY IN RH-CATALYZED HYDROGENATIONS - D-GLUCOSE-DERIVED LIGANDS FOR THE SYNTHESIS OF D-AMINO-ACIDS OR L-AMINO-ACIDS
    RAJANBABU, TV
    AYERS, TA
    CASALNUOVO, AL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (09) : 4101 - 4102
  • [5] Modular Synthesis of Highly Substituted 3-Azapyrroles by Rh(II)-Catalyzed N-H Bond Insertion and Cyclodehydration
    Williams, Matthew B.
    Boyer, Alistair
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (24): : 16139 - 16156
  • [6] Palladium catalyzed N-H bond insertion and intramolecular cyclization cascade: the divergent synthesis of heterocyclics
    Ding, Dong
    Liu, Gang
    Xu, Guangyang
    Li, Jian
    Wang, Guoping
    Sun, Jiangtao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (16) : 2533 - 2537
  • [7] N-Boc-α-diazo glutarimide as efficient reagent for assembling N-heterocycle-glutarimide diads via Rh(II)-catalyzed N-H insertion reaction
    Kantin, Grigory
    Golubev, Pavel
    Sapegin, Alexander
    Bunev, Alexander
    Dar'in, Dmitry
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2023, 19 : 1841 - 1848
  • [8] BIS (ACETYLACETONATO) COPPER(II) CATALYZED INSERTION OF BENZOYLPHENYLCARBENE INTO SECONDARY AMINO N-H BOND
    SINGH, GS
    NATIONAL ACADEMY SCIENCE LETTERS-INDIA, 1991, 14 (11): : 445 - 446
  • [9] Copper-catalyzed asymmetric N-H insertion reactions: Couplings of diazo compounds with carbamates to generate α-amino acids
    Lee, Elaine C.
    Fu, Gregory C.
    Journal of the American Chemical Society, 2007, 129 (40): : 12066 - 12067
  • [10] Copper-catalyzed asymmetric N-H insertion reactions:: Couplings of diazo compounds with carbamates to generate α-amino acids
    Lee, Elaine C.
    Fu, Gregory C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (40) : 12066 - +
12345