Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents

Shermin S Goh; Sureshbabu Guduguntla; Takashi Kikuchi; Martin Lutz; Edwin Otten; Makoto Fujita; Ben L Feringa

doi:10.1021/jacs.8b02992

Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents

Shermin S Goh, Sureshbabu Guduguntla, Takashi Kikuchi, Martin Lutz, Edwin Otten, Makoto Fujita, Ben L Feringa^*

^*Corresponding author for this work

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

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Abstract

The highly regio- and enantioselective (up to >99:1 dr, up to 99:1 er) desymmetrization of meso-1,4-dibromocycloalk-2-enes using asymmetric allylic substitution with organolithium reagents to afford enantioenriched bromocycloalkenes (ring size of 5 to 7) has been achieved. The cycloheptene products undergo an unusual ring contraction. The synthetic versatility of this Cu(I)-catalyzed reaction is demonstrated by the concise stereocontrolled preparation of cyclic amino alcohols, which are privileged chiral structures in natural products and pharmaceuticals and widely used in synthesis and catalysis.

Original language	English
Pages (from-to)	7052-7055
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	140
Issue number	23
DOIs	https://doi.org/10.1021/jacs.8b02992
Publication status	Published - 13-Jun-2018

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10.1021/jacs.8b02992Licence: CC BY-NC-ND

Desymmetrization of meso -Dibromocycloalkenes through Copper(I)- Catalyzed Asymmetric Allylic Substitution with Organolithium ReagentsFinal publisher's version, 1.06 MBLicence: CC BY-NC-ND

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CCDC 1575122: Experimental Crystal Structure Determination
Goh, S. S. (Contributor), Guduguntla, S. (Contributor), Kikuchi, T. (Contributor), Lutz, M. (Contributor), Otten, E. (Contributor), Fujita, M. (Contributor) & Feringa, B. L. (Contributor), University of Groningen, 23-Nov-2017
DOI: 10.5517/ccdc.csd.cc1pw1d0
Dataset
CCDC 1577535: Experimental Crystal Structure Determination
Goh, S. S. (Contributor), Guduguntla, S. (Contributor), Kikuchi, T. (Contributor), Lutz, M. (Contributor), Otten, E. (Contributor), Fujita, M. (Contributor) & Feringa, B. L. (Contributor), University of Groningen, 2-Oct-2017
DOI: 10.5517/ccdc.csd.cc1pyk7f
Dataset

Cite this

@article{dc4093535cc94a30adb3873bb85dd61b,

title = "Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents",

abstract = "The highly regio- and enantioselective (up to >99:1 dr, up to 99:1 er) desymmetrization of meso-1,4-dibromocycloalk-2-enes using asymmetric allylic substitution with organolithium reagents to afford enantioenriched bromocycloalkenes (ring size of 5 to 7) has been achieved. The cycloheptene products undergo an unusual ring contraction. The synthetic versatility of this Cu(I)-catalyzed reaction is demonstrated by the concise stereocontrolled preparation of cyclic amino alcohols, which are privileged chiral structures in natural products and pharmaceuticals and widely used in synthesis and catalysis.",

author = "Goh, {Shermin S} and Sureshbabu Guduguntla and Takashi Kikuchi and Martin Lutz and Edwin Otten and Makoto Fujita and Feringa, {Ben L}",

year = "2018",

month = jun,

day = "13",

doi = "10.1021/jacs.8b02992",

language = "English",

volume = "140",

pages = "7052--7055",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "AMER CHEMICAL SOC",

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}

Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents. / Goh, Shermin S; Guduguntla, Sureshbabu; Kikuchi, Takashi et al.
In: Journal of the American Chemical Society, Vol. 140, No. 23, 13.06.2018, p. 7052-7055.

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

TY - JOUR

T1 - Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents

AU - Goh, Shermin S

AU - Guduguntla, Sureshbabu

AU - Kikuchi, Takashi

AU - Lutz, Martin

AU - Otten, Edwin

AU - Fujita, Makoto

AU - Feringa, Ben L

PY - 2018/6/13

Y1 - 2018/6/13

N2 - The highly regio- and enantioselective (up to >99:1 dr, up to 99:1 er) desymmetrization of meso-1,4-dibromocycloalk-2-enes using asymmetric allylic substitution with organolithium reagents to afford enantioenriched bromocycloalkenes (ring size of 5 to 7) has been achieved. The cycloheptene products undergo an unusual ring contraction. The synthetic versatility of this Cu(I)-catalyzed reaction is demonstrated by the concise stereocontrolled preparation of cyclic amino alcohols, which are privileged chiral structures in natural products and pharmaceuticals and widely used in synthesis and catalysis.

AB - The highly regio- and enantioselective (up to >99:1 dr, up to 99:1 er) desymmetrization of meso-1,4-dibromocycloalk-2-enes using asymmetric allylic substitution with organolithium reagents to afford enantioenriched bromocycloalkenes (ring size of 5 to 7) has been achieved. The cycloheptene products undergo an unusual ring contraction. The synthetic versatility of this Cu(I)-catalyzed reaction is demonstrated by the concise stereocontrolled preparation of cyclic amino alcohols, which are privileged chiral structures in natural products and pharmaceuticals and widely used in synthesis and catalysis.

U2 - 10.1021/jacs.8b02992

DO - 10.1021/jacs.8b02992

M3 - Article

C2 - 29790736

SN - 0002-7863

VL - 140

SP - 7052

EP - 7055

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 23

ER -

Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents

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CCDC 1575122: Experimental Crystal Structure Determination

CCDC 1577535: Experimental Crystal Structure Determination

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