Intramolecular [3+2] nitrone cycloaddition reaction: highly regio and diastereoselective synthesis of bicyclo[3.2.1]octane scaffolds

被引：4
作者：
Bakthadoss, Manickam [1 ]
Mushaf, Mohammad [1 ]
机构：
[1] Pondicherry Univ, Dept Chem, Pondicherry 605014, India
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 47期
关键词：
X=Y-ZH SYSTEMS; POTENTIAL 1,3-DIPOLES; N; N-DISUBSTITUTED HYDROXYLAMINES; STEREOSELECTIVE-SYNTHESIS; HYDROGEN-PEROXIDE; CLASS-2; PROCESSES; STERIC FACTORS; DERIVATIVES; CONSTRUCTION; GENERATION;
D O I：
10.1039/d0ob01960g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A regio and diastereoselective strategy has been developed for the synthesis of complex bicyclo[3.2.1]octane scaffolds from the reaction of readily accessible vinylogous carbonates with N-substituted hydroxylamine hydrochlorides via intramolecular 1,3-dipolar nitrone cycloaddition reaction. Wide varieties of bicyclic isoxazolidines were synthesized in high yields under catalyst free conditions through a highly efficient and operationally simple protocol.
引用
收藏
页码：9653 / 9659
页数：7
相关论文
共 72 条
  • [1] [Anonymous], 2003, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products
  • [2] A Direct Cycloaminative Approach to Imidazole Derivatives via Dual C-H Functionalization
    Arepally, Sagar
    Babu, Venkata Nagarjuna
    Bakthadoss, Manickam
    Sharada, Duddu S.
    [J]. ORGANIC LETTERS, 2017, 19 (19) : 5014 - 5017
  • [3] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .33. GENERATION OF NITRONES FROM OXIMES - TANDEM MICHAEL ADDITION-1,3-DIPOLAR CYCLOADDITION REACTIONS - CLASS-2 PROCESSES IN WHICH THE DIPOLAROPHILE IS LOCATED WITHIN THE OXIME
    ARMSTRONG, P
    GRIGG, R
    HEANEY, F
    SURENDRAKUMAR, S
    WARNOCK, WJ
    [J]. TETRAHEDRON, 1991, 47 (25) : 4495 - 4518
  • [4] Arrighi M, 2001, SYNTHESIS-STUTTGART, P473
  • [5] Bakthadoss M., 2013, SYNTHESIS-STUTTGART, P237
  • [6] Assembly of Highly Functionalized Chromenopyranpyrazoles via Multicomponent Quadruple Domino Reaction (MCQDR)
    Bakthadoss, Manickam
    Deyaraj, Anthonisamy
    Mushaf, Mohammad
    [J]. CHEMISTRYSELECT, 2019, 4 (40): : 11822 - 11825
  • [7] A rearrangement involving a solid-state melt reaction for the synthesis of multifunctional tetrasubstituted olefins
    Bakthadoss, Manickam
    Raman, Selvakumar
    Mushaf, Mohammad
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (19) : 4767 - 4773
  • [8] A distal vinyl shift (DVS) through quadruple domino reaction: synthesis of N-vinyl benzoheterocyclic scaffolds
    Bakthadoss, Manickam
    Mushaf, Mohammad
    [J]. RSC ADVANCES, 2018, 8 (22): : 12152 - 12156
  • [9] One-Pot Synthesis of Benzothiazole-Tethered Chromanones/Coumarins via Claisen Rearrangement Using the Solid State Melt Reaction
    Bakthadoss, Manickam
    Selvakumar, Raman
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (08) : 3391 - 3399
  • [10] Synthesis of highly diversified 1,2,3-triazole derivatives via domino [3+2] azide cycloaddition and denitration reaction sequence
    Bakthadoss, Manickam
    Sivakumar, Nagappan
    Devaraj, Anthonisamy
    Kumar, Polu Vijay
    [J]. RSC ADVANCES, 2015, 5 (113) : 93447 - 93451
12345678