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Stereoselective aziridination of cyclic allylic alcohols using chloramine-T

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

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Stereoselective aziridination of cyclic allylic alcohols using chloramine-T. / Coote, Susannah C.; O'Brien, Peter; Whitwood, Adrian C.
In: Organic and Biomolecular Chemistry , Vol. 6, No. 23, 2008, p. 4299-4314.

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

Harvard

Coote, SC, O'Brien, P & Whitwood, AC 2008, 'Stereoselective aziridination of cyclic allylic alcohols using chloramine-T', Organic and Biomolecular Chemistry , vol. 6, no. 23, pp. 4299-4314. https://doi.org/10.1039/b811137e

APA

Coote, S. C., O'Brien, P., & Whitwood, A. C. (2008). Stereoselective aziridination of cyclic allylic alcohols using chloramine-T. Organic and Biomolecular Chemistry , 6(23), 4299-4314. https://doi.org/10.1039/b811137e

Vancouver

Coote SC, O'Brien P, Whitwood AC. Stereoselective aziridination of cyclic allylic alcohols using chloramine-T. Organic and Biomolecular Chemistry . 2008;6(23):4299-4314. doi: 10.1039/b811137e

Author

Coote, Susannah C. ; O'Brien, Peter ; Whitwood, Adrian C. / Stereoselective aziridination of cyclic allylic alcohols using chloramine-T. In: Organic and Biomolecular Chemistry . 2008 ; Vol. 6, No. 23. pp. 4299-4314.

Bibtex

@article{03fdc4e3b6a1466aaba95383fb23e8c6,
title = "Stereoselective aziridination of cyclic allylic alcohols using chloramine-T",
abstract = "The stereoselective aziridination of a range of cyclic allylic alcohols using two different chloramine salts (4-MeC(6)H(4)SO(2)NClNa, TsNClNa and t-BuSO(2)NClNa, BusNClNa) has been explored. The stereoselectivity of these reactions was highly dependent on the structure of the allylic alcohol and the chloramine salt. Generally, mixtures of cis- and trans-hydroxy aziridines were obtained, in which the major diastereomer was the cis- hydroxy aziridine, whilst complete cis-diastereoselectivity was observed in the aziridination of 1,3-disubstituted allylic alcohols. In each case studied, aziridination using BusNClNa gave higher cis- stereoselectivity than that observed for the same reaction using TsNClNa. Unexpectedly, application of the aziridination conditions to 1-substituted cyclopen-2-en-1-ols did not generate the aziridines. Instead, epoxy sulfonamides were obtained.",
keywords = "BETA-ALKOXY AZIRIDINES, ORGANOLITHIUM-MEDIATED CONVERSION, BROMINE-CATALYZED AZIRIDINATION, ALPHA-LITHIATION-REARRANGEMENT, REDUCTIVE ALKYLATION, NITROGEN-SOURCE, EPOXIDATION, EPOXIDES, REAGENTS, ALKENES",
author = "Coote, {Susannah C.} and Peter O'Brien and Whitwood, {Adrian C.}",
year = "2008",
doi = "10.1039/b811137e",
language = "English",
volume = "6",
pages = "4299--4314",
journal = "Organic and Biomolecular Chemistry ",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "23",

}

RIS

TY - JOUR

T1 - Stereoselective aziridination of cyclic allylic alcohols using chloramine-T

AU - Coote, Susannah C.

AU - O'Brien, Peter

AU - Whitwood, Adrian C.

PY - 2008

Y1 - 2008

N2 - The stereoselective aziridination of a range of cyclic allylic alcohols using two different chloramine salts (4-MeC(6)H(4)SO(2)NClNa, TsNClNa and t-BuSO(2)NClNa, BusNClNa) has been explored. The stereoselectivity of these reactions was highly dependent on the structure of the allylic alcohol and the chloramine salt. Generally, mixtures of cis- and trans-hydroxy aziridines were obtained, in which the major diastereomer was the cis- hydroxy aziridine, whilst complete cis-diastereoselectivity was observed in the aziridination of 1,3-disubstituted allylic alcohols. In each case studied, aziridination using BusNClNa gave higher cis- stereoselectivity than that observed for the same reaction using TsNClNa. Unexpectedly, application of the aziridination conditions to 1-substituted cyclopen-2-en-1-ols did not generate the aziridines. Instead, epoxy sulfonamides were obtained.

AB - The stereoselective aziridination of a range of cyclic allylic alcohols using two different chloramine salts (4-MeC(6)H(4)SO(2)NClNa, TsNClNa and t-BuSO(2)NClNa, BusNClNa) has been explored. The stereoselectivity of these reactions was highly dependent on the structure of the allylic alcohol and the chloramine salt. Generally, mixtures of cis- and trans-hydroxy aziridines were obtained, in which the major diastereomer was the cis- hydroxy aziridine, whilst complete cis-diastereoselectivity was observed in the aziridination of 1,3-disubstituted allylic alcohols. In each case studied, aziridination using BusNClNa gave higher cis- stereoselectivity than that observed for the same reaction using TsNClNa. Unexpectedly, application of the aziridination conditions to 1-substituted cyclopen-2-en-1-ols did not generate the aziridines. Instead, epoxy sulfonamides were obtained.

KW - BETA-ALKOXY AZIRIDINES

KW - ORGANOLITHIUM-MEDIATED CONVERSION

KW - BROMINE-CATALYZED AZIRIDINATION

KW - ALPHA-LITHIATION-REARRANGEMENT

KW - REDUCTIVE ALKYLATION

KW - NITROGEN-SOURCE

KW - EPOXIDATION

KW - EPOXIDES

KW - REAGENTS

KW - ALKENES

U2 - 10.1039/b811137e

DO - 10.1039/b811137e

M3 - Journal article

VL - 6

SP - 4299

EP - 4314

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 23

ER -