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An iron-catalysed C-C bond-forming spirocyclization cascade providing sustainable access to new 3D heterocyclic frameworks

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

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An iron-catalysed C-C bond-forming spirocyclization cascade providing sustainable access to new 3D heterocyclic frameworks. / Adams, Kirsty; Ball, Anthony K.; Birkett, James et al.
In: Nature Chemistry, Vol. 9, No. 4, 01.04.2017, p. 396-401.

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

Harvard

Adams, K, Ball, AK, Birkett, J, Brown, L, Chappell, B, Gill, DM, Lo, PKT, Patmore, NJ, Rice, CR, Ryan, J, Raubo, P & Sweeney, JB 2017, 'An iron-catalysed C-C bond-forming spirocyclization cascade providing sustainable access to new 3D heterocyclic frameworks', Nature Chemistry, vol. 9, no. 4, pp. 396-401. https://doi.org/10.1038/nchem.2670

APA

Adams, K., Ball, A. K., Birkett, J., Brown, L., Chappell, B., Gill, D. M., Lo, P. K. T., Patmore, N. J., Rice, C. R., Ryan, J., Raubo, P., & Sweeney, J. B. (2017). An iron-catalysed C-C bond-forming spirocyclization cascade providing sustainable access to new 3D heterocyclic frameworks. Nature Chemistry, 9(4), 396-401. https://doi.org/10.1038/nchem.2670

Vancouver

Adams K, Ball AK, Birkett J, Brown L, Chappell B, Gill DM et al. An iron-catalysed C-C bond-forming spirocyclization cascade providing sustainable access to new 3D heterocyclic frameworks. Nature Chemistry. 2017 Apr 1;9(4):396-401. Epub 2016 Dec 12. doi: 10.1038/nchem.2670

Author

Adams, Kirsty ; Ball, Anthony K. ; Birkett, James et al. / An iron-catalysed C-C bond-forming spirocyclization cascade providing sustainable access to new 3D heterocyclic frameworks. In: Nature Chemistry. 2017 ; Vol. 9, No. 4. pp. 396-401.

Bibtex

@article{bd0863696f2d4490b7faaf2dee912bcf,
title = "An iron-catalysed C-C bond-forming spirocyclization cascade providing sustainable access to new 3D heterocyclic frameworks",
abstract = "Heterocyclic architectures offer powerful creative possibilities to a range of chemistry end-users. This is particularly true of heterocycles containing a high proportion of sp3 -carbon atoms, which confer precise spatial definition upon chemical probes, drug substances, chiral monomers and the like. Nonetheless, simple catalytic routes to new heterocyclic cores are infrequently reported, and methods making use of biomass-accessible starting materials are also rare. Here, we demonstrate a new method allowing rapid entry to spirocyclic bis-heterocycles, in which inexpensive iron(III) catalysts mediate a highly stereoselective C-C bond-forming cyclization cascade reaction using (2-halo)aryl ethers and amines constructed using feedstock chemicals readily available from plant sources. Fe(acac) 3 mediates the deiodinative cyclization of (2-halo)aryloxy furfuranyl ethers, followed by capture of the intermediate metal species by Grignard reagents, to deliver spirocycles containing two asymmetric centres. The reactions offer potential entry to key structural motifs present in bioactive natural products.",
author = "Kirsty Adams and Ball, {Anthony K.} and James Birkett and Lee Brown and Ben Chappell and Gill, {Duncan M.} and Lo, {P. K.Tony} and Patmore, {Nathan J.} and Rice, {Craig R.} and James Ryan and Piotr Raubo and Sweeney, {Joseph B.}",
year = "2017",
month = apr,
day = "1",
doi = "10.1038/nchem.2670",
language = "English",
volume = "9",
pages = "396--401",
journal = "Nature Chemistry",
issn = "1755-4330",
publisher = "Nature Publishing Group",
number = "4",

}

RIS

TY - JOUR

T1 - An iron-catalysed C-C bond-forming spirocyclization cascade providing sustainable access to new 3D heterocyclic frameworks

AU - Adams, Kirsty

AU - Ball, Anthony K.

AU - Birkett, James

AU - Brown, Lee

AU - Chappell, Ben

AU - Gill, Duncan M.

AU - Lo, P. K.Tony

AU - Patmore, Nathan J.

AU - Rice, Craig R.

AU - Ryan, James

AU - Raubo, Piotr

AU - Sweeney, Joseph B.

PY - 2017/4/1

Y1 - 2017/4/1

N2 - Heterocyclic architectures offer powerful creative possibilities to a range of chemistry end-users. This is particularly true of heterocycles containing a high proportion of sp3 -carbon atoms, which confer precise spatial definition upon chemical probes, drug substances, chiral monomers and the like. Nonetheless, simple catalytic routes to new heterocyclic cores are infrequently reported, and methods making use of biomass-accessible starting materials are also rare. Here, we demonstrate a new method allowing rapid entry to spirocyclic bis-heterocycles, in which inexpensive iron(III) catalysts mediate a highly stereoselective C-C bond-forming cyclization cascade reaction using (2-halo)aryl ethers and amines constructed using feedstock chemicals readily available from plant sources. Fe(acac) 3 mediates the deiodinative cyclization of (2-halo)aryloxy furfuranyl ethers, followed by capture of the intermediate metal species by Grignard reagents, to deliver spirocycles containing two asymmetric centres. The reactions offer potential entry to key structural motifs present in bioactive natural products.

AB - Heterocyclic architectures offer powerful creative possibilities to a range of chemistry end-users. This is particularly true of heterocycles containing a high proportion of sp3 -carbon atoms, which confer precise spatial definition upon chemical probes, drug substances, chiral monomers and the like. Nonetheless, simple catalytic routes to new heterocyclic cores are infrequently reported, and methods making use of biomass-accessible starting materials are also rare. Here, we demonstrate a new method allowing rapid entry to spirocyclic bis-heterocycles, in which inexpensive iron(III) catalysts mediate a highly stereoselective C-C bond-forming cyclization cascade reaction using (2-halo)aryl ethers and amines constructed using feedstock chemicals readily available from plant sources. Fe(acac) 3 mediates the deiodinative cyclization of (2-halo)aryloxy furfuranyl ethers, followed by capture of the intermediate metal species by Grignard reagents, to deliver spirocycles containing two asymmetric centres. The reactions offer potential entry to key structural motifs present in bioactive natural products.

U2 - 10.1038/nchem.2670

DO - 10.1038/nchem.2670

M3 - Journal article

AN - SCOPUS:85016234249

VL - 9

SP - 396

EP - 401

JO - Nature Chemistry

JF - Nature Chemistry

SN - 1755-4330

IS - 4

ER -