π-Allyl cation cyclisations initiated by silver(I)-promoted electrocyclic ring opening of ring-fused gew-dibromocyclopropanes possessing tethered nucleophiles: The influence of chiral auxiliaries on the diastereoselectivity of cyclisations involving meso-substrates

Martin Banwell; Alison Edwards; Joanne Harvey; David Hockless; Anthony Willis

doi:10.1039/b002525i

π-Allyl cation cyclisations initiated by silver(I)-promoted electrocyclic ring opening of ring-fused gew-dibromocyclopropanes possessing tethered nucleophiles: The influence of chiral auxiliaries on the diastereoselectivity of cyclisations involving meso-substrates

Martin Banwell^*, Alison Edwards, Joanne Harvey, David Hockless, Anthony Willis

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

Abstract

The epimeric pairs of ring-fused gem-dibromocyclopropanes 17/18 and 27/28, each of which possesses an internal plane of symmetry and has a tethered carbamate moiety with an associated chiral auxiliary, react with silver perchlorate to give, in a diastereoselective manner, the corresponding pairs of azabicyclic compounds, 19/20 and 29/30 respectively.

Original language	English
Pages (from-to)	2175-2178
Number of pages	4
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	14
DOIs	https://doi.org/10.1039/b002525i
Publication status	Published - 2000

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Banwell, M., Edwards, A., Harvey, J., Hockless, D., & Willis, A. (2000). π-Allyl cation cyclisations initiated by silver(I)-promoted electrocyclic ring opening of ring-fused gew-dibromocyclopropanes possessing tethered nucleophiles: The influence of chiral auxiliaries on the diastereoselectivity of cyclisations involving meso-substrates. Journal of the Chemical Society, Perkin Transactions 1, (14), 2175-2178. https://doi.org/10.1039/b002525i

Banwell, Martin ; Edwards, Alison ; Harvey, Joanne et al. / π-Allyl cation cyclisations initiated by silver(I)-promoted electrocyclic ring opening of ring-fused gew-dibromocyclopropanes possessing tethered nucleophiles : The influence of chiral auxiliaries on the diastereoselectivity of cyclisations involving meso-substrates. In: Journal of the Chemical Society, Perkin Transactions 1. 2000 ; No. 14. pp. 2175-2178.

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title = "π-Allyl cation cyclisations initiated by silver(I)-promoted electrocyclic ring opening of ring-fused gew-dibromocyclopropanes possessing tethered nucleophiles: The influence of chiral auxiliaries on the diastereoselectivity of cyclisations involving meso-substrates",

abstract = "The epimeric pairs of ring-fused gem-dibromocyclopropanes 17/18 and 27/28, each of which possesses an internal plane of symmetry and has a tethered carbamate moiety with an associated chiral auxiliary, react with silver perchlorate to give, in a diastereoselective manner, the corresponding pairs of azabicyclic compounds, 19/20 and 29/30 respectively.",

author = "Martin Banwell and Alison Edwards and Joanne Harvey and David Hockless and Anthony Willis",

year = "2000",

doi = "10.1039/b002525i",

language = "English",

pages = "2175--2178",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1472-7781",

publisher = "Chemical Society",

number = "14",

}

Banwell, M, Edwards, A, Harvey, J, Hockless, D & Willis, A 2000, 'π-Allyl cation cyclisations initiated by silver(I)-promoted electrocyclic ring opening of ring-fused gew-dibromocyclopropanes possessing tethered nucleophiles: The influence of chiral auxiliaries on the diastereoselectivity of cyclisations involving meso-substrates', Journal of the Chemical Society, Perkin Transactions 1, no. 14, pp. 2175-2178. https://doi.org/10.1039/b002525i

π-Allyl cation cyclisations initiated by silver(I)-promoted electrocyclic ring opening of ring-fused gew-dibromocyclopropanes possessing tethered nucleophiles: The influence of chiral auxiliaries on the diastereoselectivity of cyclisations involving meso-substrates. / Banwell, Martin; Edwards, Alison; Harvey, Joanne et al.
In: Journal of the Chemical Society, Perkin Transactions 1, No. 14, 2000, p. 2175-2178.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - π-Allyl cation cyclisations initiated by silver(I)-promoted electrocyclic ring opening of ring-fused gew-dibromocyclopropanes possessing tethered nucleophiles

T2 - The influence of chiral auxiliaries on the diastereoselectivity of cyclisations involving meso-substrates

AU - Banwell, Martin

AU - Edwards, Alison

AU - Harvey, Joanne

AU - Hockless, David

AU - Willis, Anthony

PY - 2000

Y1 - 2000

N2 - The epimeric pairs of ring-fused gem-dibromocyclopropanes 17/18 and 27/28, each of which possesses an internal plane of symmetry and has a tethered carbamate moiety with an associated chiral auxiliary, react with silver perchlorate to give, in a diastereoselective manner, the corresponding pairs of azabicyclic compounds, 19/20 and 29/30 respectively.

AB - The epimeric pairs of ring-fused gem-dibromocyclopropanes 17/18 and 27/28, each of which possesses an internal plane of symmetry and has a tethered carbamate moiety with an associated chiral auxiliary, react with silver perchlorate to give, in a diastereoselective manner, the corresponding pairs of azabicyclic compounds, 19/20 and 29/30 respectively.

UR - https://www.scopus.com/pages/publications/0034698455

U2 - 10.1039/b002525i

DO - 10.1039/b002525i

M3 - Article

SN - 1472-7781

SP - 2175

EP - 2178

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 14

ER -

Banwell M, Edwards A, Harvey J, Hockless D, Willis A. π-Allyl cation cyclisations initiated by silver(I)-promoted electrocyclic ring opening of ring-fused gew-dibromocyclopropanes possessing tethered nucleophiles: The influence of chiral auxiliaries on the diastereoselectivity of cyclisations involving meso-substrates. Journal of the Chemical Society, Perkin Transactions 1. 2000;(14):2175-2178. doi: 10.1039/b002525i

π-Allyl cation cyclisations initiated by silver(I)-promoted electrocyclic ring opening of ring-fused gew-dibromocyclopropanes possessing tethered nucleophiles: The influence of chiral auxiliaries on the diastereoselectivity of cyclisations involving meso-substrates

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