Synthesis of 3-Nitropyrrolidines via Dipolar Cycloaddition Reactions Using a Modular Flow Reactor

被引:44
作者
Baumann, Marcus [1 ]
Baxendale, Ian R. [1 ]
Ley, Steven V. [1 ]
机构
[1] Univ Cambridge, Dept Chem, Innovat Technol Ctr, Cambridge CB2 1EW, England
基金
英国工程与自然科学研究理事会;
关键词
microreactor; flow chemistry; pyrrolidine; dipolar cycloaddition; solid-supported reagents; MULTISTEP SYNTHESIS; ORGANIC-SYNTHESIS; MICROREACTOR; CHEMISTRY;
D O I
10.1055/s-0029-1219344
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The generation and subsequent use of unstabilised azomethine ylides in dipolar cycloaddition reactions within a flow microreactor is demonstrated. The 3-nitropyrrolidines produced were furthermore subjected to chemoselective hydrogenation reactions using the H-Cube (R) system. To ensure product purities in excess of 90-95%, immobilised scavengers were successfully employed.
引用
收藏
页码:749 / 752
页数:4
相关论文
共 44 条
[1]   The use of diethylaminosulfur trifluoride (DAST) for fluorination in a continuous-flow microreactor [J].
Baumann, Marcus ;
Baxendale, Ian R. ;
Ley, Steven V. .
SYNLETT, 2008, (14) :2111-2114
[2]   Azide monoliths as convenient flow reactors for efficient Curtius rearrangement reactions [J].
Baumann, Marcus ;
Baxendale, Ian R. ;
Ley, Steven V. ;
Nikbin, Nikzad ;
Smith, Christopher D. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (09) :1587-1593
[3]   A modular flow reactor for performing Curtius rearrangements as a continuous flow process [J].
Baumann, Marcus ;
Baxendale, Ian R. ;
Ley, Steven V. ;
Nikbin, Nikzad ;
Smith, Christopher D. ;
Tierney, Jason P. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (09) :1577-1586
[4]   Fully automated continuous flow synthesis of 4,5-disubstituted oxazoles [J].
Baumann, Marcus ;
Baxendale, Ian R. ;
Ley, Steven V. ;
Smith, Christoper D. ;
Tranmer, Geoffrey K. .
ORGANIC LETTERS, 2006, 8 (23) :5231-5234
[5]   Development of fluorination methods using continuous-flow microreactors [J].
Baumann, Marcus ;
Baxendale, Ian R. ;
Martin, Laetitia J. ;
Ley, Steven V. .
TETRAHEDRON, 2009, 65 (33) :6611-6625
[6]   A Bifurcated Pathway to Thiazoles and Imidazoles Using a Modular Flow Microreactor [J].
Baxendale, Ian R. ;
Ley, Steven V. ;
Smith, Christopher D. ;
Tamborini, Lucia ;
Voica, Ana-Florina .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (06) :851-857
[7]   Pharmaceutical strategy and innovation: An academics perspective [J].
Baxendale, Ian R. ;
Hayward, John J. ;
Ley, Steven V. ;
Tranmer, Geoffrey K. .
CHEMMEDCHEM, 2007, 2 (06) :768-788
[8]   A flow reactor process for the synthesis of peptides utilizing immobilized reagents, scavengers and catch and release protocols [J].
Baxendale, Ian R. ;
Ley, Steven V. ;
Smith, Christopher D. ;
Tranmer, Geoffrey K. .
CHEMICAL COMMUNICATIONS, 2006, (46) :4835-4837
[9]  
Baxendale IR, 2006, CHIM OGGI, V24, P41
[10]   A flow process for the multi-step synthesis of the alkaloid natural product oxomaritidine: a new paradigm for molecular assembly [J].
Baxendale, Ian R. ;
Deeley, Jon ;
Griffiths-Jones, Charlotte M. ;
Ley, Steven V. ;
Saaby, Steen ;
Tranmer, Geoffrey K. .
CHEMICAL COMMUNICATIONS, 2006, (24) :2566-2568