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

来源：

SYNLETT | 2010年 / 05期

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

页码：749 / 752

页数：4

共 44 条

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Baumann, Marcus
Baxendale, Ian R.
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[2] Azide monoliths as convenient flow reactors for efficient Curtius rearrangement reactions
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[4] Fully automated continuous flow synthesis of 4,5-disubstituted oxazoles
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[J]. TETRAHEDRON, 2009, 65 (33) : 6611 - 6625
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Voica, Ana-Florina
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (06): : 851 - 857
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[J]. 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
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Ley, Steven V.
Smith, Christopher D.
Tranmer, Geoffrey K.
[J]. 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
Baxendale, Ian R.
Deeley, Jon
Griffiths-Jones, Charlotte M.
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