Details
| Original language | English |
|---|---|
| Pages (from-to) | 1297-1316 |
| Number of pages | 20 |
| Journal | Heterocycles |
| Volume | 82 |
| Issue number | 2 |
| Publication status | Published - 2 Aug 2010 |
Abstract
We expand upon recent results concerning dipolar cycloaddition reactions of unstabilized azomethine ylids with nitro alkenes to generate 3-nitropyrrolidines via a flow chemistry sequence. This new work describes the development of a three-component coupling reaction between glycine esters, aldehydes and nitro alkenes. In order to further demonstrate the utility of flow technology in concert with heterogeneous reagents and scavengers for complex reaction sequences an in-line oxidation resulting in the conversion of tetra-substituted pyrrolidines to their pyrrole congeners has been developed.
ASJC Scopus subject areas
- Chemistry(all)
- Analytical Chemistry
- Pharmacology, Toxicology and Pharmaceutics(all)
- Pharmacology
- Chemistry(all)
- Organic Chemistry
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In: Heterocycles, Vol. 82, No. 2, 02.08.2010, p. 1297-1316.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis of highly substituted nitropyrrolidines, nitropyrrolizines and nitropyrroles via multicomponent-multistep sequences within a flow reactor
AU - Baumann, Marcus
AU - Baxendale, Ian R.
AU - Kirschning, Andreas
AU - Ley, Steven V.
AU - Wegner, Jens
PY - 2010/8/2
Y1 - 2010/8/2
N2 - We expand upon recent results concerning dipolar cycloaddition reactions of unstabilized azomethine ylids with nitro alkenes to generate 3-nitropyrrolidines via a flow chemistry sequence. This new work describes the development of a three-component coupling reaction between glycine esters, aldehydes and nitro alkenes. In order to further demonstrate the utility of flow technology in concert with heterogeneous reagents and scavengers for complex reaction sequences an in-line oxidation resulting in the conversion of tetra-substituted pyrrolidines to their pyrrole congeners has been developed.
AB - We expand upon recent results concerning dipolar cycloaddition reactions of unstabilized azomethine ylids with nitro alkenes to generate 3-nitropyrrolidines via a flow chemistry sequence. This new work describes the development of a three-component coupling reaction between glycine esters, aldehydes and nitro alkenes. In order to further demonstrate the utility of flow technology in concert with heterogeneous reagents and scavengers for complex reaction sequences an in-line oxidation resulting in the conversion of tetra-substituted pyrrolidines to their pyrrole congeners has been developed.
UR - http://www.scopus.com/inward/record.url?scp=79952761078&partnerID=8YFLogxK
U2 - 10.3987/COM-10-S(E)77
DO - 10.3987/COM-10-S(E)77
M3 - Article
AN - SCOPUS:79952761078
VL - 82
SP - 1297
EP - 1316
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 2
ER -