Journal article

Asymmetric conjugate additions of alkylzirconocenes to cyclopent-4-ene-1,3-dione monoacetals.

Abstract:: Copper-catalyzed asymmetric conjugate additions are powerful reactions that allow the formation of single-enantiomer building blocks in a few steps. However, highly enantioselective conjugate addition to five-membered-ring substrates is more challenging and is often neglected. Here, we report catalytic asymmetric 1,4-addition of alkylzirconocenes, formed in situ from readily available alkenes, to cyclopent-4-ene-1,3-dione monoacetals. Good to high enantioselectivities are observed and the procedure tolerates various functional groups.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Rideau, E., Masing, F., & Fletcher, S. (2015). Asymmetric conjugate additions of alkylzirconocenes to cyclopent-4-ene-1,3-dione monoacetals. Synthesis, 47(15), 2217–2222.

MLA Style

Rideau, E., et al. “Asymmetric Conjugate Additions of Alkylzirconocenes to Cyclopent-4-Ene-1,3-Dione Monoacetals.” Synthesis, Publisher's version, vol. 47, no. 15, 2015, pp. 2217–22.

Chicago Style

Rideau, E, F Masing, and S Fletcher. 2015. “Asymmetric Conjugate Additions of Alkylzirconocenes to Cyclopent-4-Ene-1,3-Dione Monoacetals.” Synthesis 47 (15): 2217–22.
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Publisher copy:: 10.1055/s-0034-1379928

Authors

+ Rideau, E More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Research group:: Prof. Stephen Fletcher Group
Oxford college:: Lincoln College
Role:: Author

+ Masing, F More by this author

Institution:: University of Oxford
Role:: Author

+ Fletcher, S More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Oxford college:: Keble College
Role:: Principal Investigator (PI), Author

+ Engineering and Physical Sciences Research Council More from this funder

Funding agency for:: Rideau, E
Grant:: EP/H003711/1

Journal:: Synthesis More from this journal
Volume:: 47
Issue:: 15
Pages:: 2217-2222
Publication date:: 2015-01-01
Edition:: Publisher's version
DOI:: 10.1055/s-0034-1379928
ISSN:: 0039-7881

Language:: English
Keywords:: copper

asymmetric catalysis

acetals

organometallic reagents

addition reactions
Subjects:: Organic chemistry

Organic synthesis

Organometallic Chemistry

Catalysis
UUID:: uuid:fd36f602-69e3-4814-bbdf-5e7e4208bcbb
Local pid:: ora:12238
Deposit date:: 2015-09-14

Terms of use

Copyright holder:: Thieme Publishing
Copyright date:: 2015

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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