Scale-Up of Flow-Assisted Synthesis of C2-Symmetric Chiral PyBox Ligands

被引:13
作者
Battilocchio, Claudio [2 ,3 ]
Baumann, Marcus [2 ]
Baxendale, Ian R. [2 ]
Biava, Mariangela [3 ]
Kitching, Matthew O. [2 ]
Ley, Steven V. [2 ]
Martin, Rainer E. [1 ]
Ohnmacht, Stephan A. [1 ]
Tappin, Nicholas D. C. [2 ]
机构
[1] F Hoffmann La Roche Ltd, Div Pharmaceut, Chem Technol & Innovat, CH-4070 Basel, Switzerland
[2] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
[3] Univ Roma La Sapienza, Dept Pharmaceut Chem & Technol, Rome, Italy
来源
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 04期
基金
英国工程与自然科学研究理事会;
关键词
ligands; macrocycles; flow chemistry; solid-supported reagent; asymmetric synthesis; scale up; POLYUREA-ENCAPSULATED PALLADIUM; POLYMER-SUPPORTED REAGENTS; ORGANIC-SYNTHESIS; CATALYSTS; EFFICIENT; PYRIDINE-BIS(OXAZOLINE); SCAVENGERS; CHEMISTRY; IMMOBILIZATION; PARALLEL;
D O I
10.1055/s-0031-1289676
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of PyBox ligands were prepared from commercially available chelidonic acid by a multistep flow sequence using mesoreactor technology. A chloro group introduced onto the ligand scaffold was subsequently exploited to give amine derivatives ready for immobilization through microencapsulation technologies.
引用
收藏
页码:635 / 647
页数:13
相关论文
共 72 条
  • [1] Multistep reactions using microreactor chemistry
    Ahmed-Omer, Batoul
    Barrow, David A.
    Wirth, Thomas
    [J]. ARKIVOC, 2011, : 26 - 36
  • [2] "Microencapsulated" and Related Catalysts for Organic Chemistry and Organic Synthesis
    Akiyama, Ryo
    Kobayashi, Shu
    [J]. CHEMICAL REVIEWS, 2009, 109 (02) : 594 - 642
  • [3] Batoul A.-O., 2011, ORG BIOMOL CHEM, V9, P3854
  • [4] The use of diethylaminosulfur trifluoride (DAST) for fluorination in a continuous-flow microreactor
    Baumann, Marcus
    Baxendale, Ian R.
    Ley, Steven V.
    [J]. SYNLETT, 2008, (14) : 2111 - 2114
  • [5] Azide monoliths as convenient flow reactors for efficient Curtius rearrangement reactions
    Baumann, Marcus
    Baxendale, Ian R.
    Ley, Steven V.
    Nikbin, Nikzad
    Smith, Christopher D.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (09) : 1587 - 1593
  • [6] A modular flow reactor for performing Curtius rearrangements as a continuous flow process
    Baumann, Marcus
    Baxendale, Ian R.
    Ley, Steven V.
    Nikbin, Nikzad
    Smith, Christopher D.
    Tierney, Jason P.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (09) : 1577 - 1586
  • [7] SYNTHESIS OF HIGHLY SUBSTITUTED NITROPYRROLIDINES, NITROPYRROLIZINES AND NITROPYRROLES VIA MULTICOMPONENT-MULTISTEP SEQUENCES WITHIN A FLOW REACTOR
    Baumann, Marcus
    Baxendale, Ian R.
    Kirschning, Andreas
    Ley, Steven V.
    Wegner, Jens
    [J]. HETEROCYCLES, 2011, 82 (02) : 1297 - +
  • [8] Development of fluorination methods using continuous-flow microreactors
    Baumann, Marcus
    Baxendale, Ian R.
    Martin, Laetitia J.
    Ley, Steven V.
    [J]. TETRAHEDRON, 2009, 65 (33) : 6611 - 6625
  • [9] Microwave-assisted Suzuki coupling reactions with an encapsulated palladium catalyst for batch and continuous-flow transformations
    Baxendale, Ian R.
    Griffiths-Jones, Charlotte M.
    Ley, Steven V.
    Tranmer, Geoffrey K.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (16) : 4407 - 4416
  • [10] A flow process for the multi-step synthesis of the alkaloid natural product oxomaritidine: a new paradigm for molecular assembly
    Baxendale, Ian R.
    Deeley, Jon
    Griffiths-Jones, Charlotte M.
    Ley, Steven V.
    Saaby, Steen
    Tranmer, Geoffrey K.
    [J]. CHEMICAL COMMUNICATIONS, 2006, (24) : 2566 - 2568