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Unexpected products from the attempted organolithium-mediated conversion of beta-methoxy aziridines into allylic amines

Research output: Contribution to Journal/Magazine › Journal article › peer-review

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Unexpected products from the attempted organolithium-mediated conversion of beta-methoxy aziridines into allylic amines. / Coote, Susannah C.; O'Brien, Peter.
In: Tetrahedron Letters, Vol. 51, No. 4, 27.01.2010, p. 588-590.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Coote, SC & O'Brien, P 2010, 'Unexpected products from the attempted organolithium-mediated conversion of beta-methoxy aziridines into allylic amines', Tetrahedron Letters, vol. 51, no. 4, pp. 588-590. https://doi.org/10.1016/j.tetlet.2009.11.059

APA

Coote, S. C., & O'Brien, P. (2010). Unexpected products from the attempted organolithium-mediated conversion of beta-methoxy aziridines into allylic amines. Tetrahedron Letters, 51(4), 588-590. https://doi.org/10.1016/j.tetlet.2009.11.059

Vancouver

Coote SC, O'Brien P. Unexpected products from the attempted organolithium-mediated conversion of beta-methoxy aziridines into allylic amines. Tetrahedron Letters. 2010 Jan 27;51(4):588-590. doi: 10.1016/j.tetlet.2009.11.059

Author

Coote, Susannah C. ; O'Brien, Peter. / Unexpected products from the attempted organolithium-mediated conversion of beta-methoxy aziridines into allylic amines. In: Tetrahedron Letters. 2010 ; Vol. 51, No. 4. pp. 588-590.

Bibtex

@article{698374e8436e4fcdab4921f291a54b73,
title = "Unexpected products from the attempted organolithium-mediated conversion of beta-methoxy aziridines into allylic amines",
abstract = "The organolithium-mediated conversion of cyclic trans-p-methoxy aziridines and cis-beta-methoxy aziridines with a tertiary alkoxy group adjacent to the aziridine into the corresponding substituted allylic sulfonamides is reported. In all cases, unexpected products were observed and the reactivity was completely different from other related cis-beta-methoxy aziridines. The product distributions are highly dependent on the organolithium reagent employed and the structure of the methoxy aziridine Thus, together with our previous reports, the full scope and limitations of this approach to allylic sulfonamides are established. ",
keywords = "ALPHA-LITHIATION-REARRANGEMENT, ALKOXY AZIRIDINES, REDUCTIVE ALKYLATION, SULFONAMIDES, EPOXIDES, ALCOHOLS, ROUTE",
author = "Coote, {Susannah C.} and Peter O'Brien",
year = "2010",
month = jan,
day = "27",
doi = "10.1016/j.tetlet.2009.11.059",
language = "English",
volume = "51",
pages = "588--590",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Ltd",
number = "4",

}

RIS

TY - JOUR

T1 - Unexpected products from the attempted organolithium-mediated conversion of beta-methoxy aziridines into allylic amines

AU - Coote, Susannah C.

AU - O'Brien, Peter

PY - 2010/1/27

Y1 - 2010/1/27

N2 - The organolithium-mediated conversion of cyclic trans-p-methoxy aziridines and cis-beta-methoxy aziridines with a tertiary alkoxy group adjacent to the aziridine into the corresponding substituted allylic sulfonamides is reported. In all cases, unexpected products were observed and the reactivity was completely different from other related cis-beta-methoxy aziridines. The product distributions are highly dependent on the organolithium reagent employed and the structure of the methoxy aziridine Thus, together with our previous reports, the full scope and limitations of this approach to allylic sulfonamides are established. 

AB - The organolithium-mediated conversion of cyclic trans-p-methoxy aziridines and cis-beta-methoxy aziridines with a tertiary alkoxy group adjacent to the aziridine into the corresponding substituted allylic sulfonamides is reported. In all cases, unexpected products were observed and the reactivity was completely different from other related cis-beta-methoxy aziridines. The product distributions are highly dependent on the organolithium reagent employed and the structure of the methoxy aziridine Thus, together with our previous reports, the full scope and limitations of this approach to allylic sulfonamides are established. 

KW - ALPHA-LITHIATION-REARRANGEMENT

KW - ALKOXY AZIRIDINES

KW - REDUCTIVE ALKYLATION

KW - SULFONAMIDES

KW - EPOXIDES

KW - ALCOHOLS

KW - ROUTE

U2 - 10.1016/j.tetlet.2009.11.059

DO - 10.1016/j.tetlet.2009.11.059

M3 - Journal article

VL - 51

SP - 588

EP - 590

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 4

ER -