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Generation and electrophilic substitution reactions of 3-lithio-2-methyleneaziridines
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Montagne, Cyril, Prevost, Natacha, Shiers, Jason J., Prie, Gildas, Rahman, Sabitur, Hayes, Jerome F. and Shipman, Michael. (2006) Generation and electrophilic substitution reactions of 3-lithio-2-methyleneaziridines. Tetrahedron, Vol.62 (No.36). pp. 8447-8457. ISSN 0040-4020
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Official URL: http://dx.doi.org/10.1016/j.tet.2006.06.083
Abstract
2-Methyleneaziridinyl anions can be produced by selective deprotonation of the parent aziridine at C-3 using sec-BuLi/TMEDA. Subsequent reaction with a wide variety of electrophiles including MeI, ICH2CH2CH2CH2Cl, PhCH2Br, allyl bromide, Me3SiCl, Bu3SnCl, PhCHO and Ph2CO provides the corresponding C-3 substituted derivatives in moderate to good yields (43-91%). In the case of homochiral methyleneaziridines bearing an (S)-alpha-methylbenzyl group on nitrogen, high levels of diastereocontrol (up to 90%de) can be achieved in this lithiation/alkylation sequence. (c) 2006 Elsevier Ltd. All rights reserved.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Chemistry |
| Journal or Publication Title: | Tetrahedron |
| Publisher: | Pergamon |
| ISSN: | 0040-4020 |
| Date: | 4 September 2006 |
| Volume: | Vol.62 |
| Number: | No.36 |
| Number of Pages: | 11 |
| Page Range: | pp. 8447-8457 |
| Identification Number: | 10.1016/j.tet.2006.06.083 |
| Status: | Peer Reviewed |
| Publication Status: | Published |
| Access rights to Published version: | Restricted or Subscription Access |
| URI: | http://wrap.warwick.ac.uk/id/eprint/33136 |
Data sourced from Thomson Reuters' Web of Knowledge
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