Journal article

Conjugate addition of organocopper reagents to gamma-alkoxybutenolides and application to the synthesis of non-racemic alkyl cyclopentenones.

Abstract:: Simple organocopper reagents are shown to undergo anti-stereoselective 1,4-addition to menthyloxy-substituted lactone 1 in the presence of BF3.OEt2; the Lewis acid causes partial epimerisation of the acetal centre after conjugate addition. Enolate alkylation of the adducts leads to di- and trisubstituted lactones that are converted, in favourable cases, into di- and trisubstituted cyclopentenones.

Publication status:: Published

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APA Style

Robertson, J., Menard, M., Ford, R., & Bell, S. (2004). Conjugate addition of organocopper reagents to gamma-alkoxybutenolides and application to the synthesis of non-racemic alkyl cyclopentenones. Organic and Biomolecular Chemistry, 2(20), 2988–2997.

MLA Style

Robertson, J., et al. “Conjugate Addition of Organocopper Reagents to Gamma-Alkoxybutenolides and Application to the Synthesis of Non-Racemic Alkyl Cyclopentenones.” Organic and Biomolecular Chemistry, vol. 2, no. 20, 2004, pp. 2988–97.

Chicago Style

Robertson, J, M Menard, R Ford, and S Bell. 2004. “Conjugate Addition of Organocopper Reagents to Gamma-Alkoxybutenolides and Application to the Synthesis of Non-Racemic Alkyl Cyclopentenones.” Organic and Biomolecular Chemistry 2 (20): 2988–97.
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Publisher copy:: 10.1039/b408255a

Authors

+ Robertson, J More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

+ Menard, M More by this author

Role:: Author

+ Ford, R More by this author

Role:: Author

+ Bell, S More by this author

Role:: Author

Journal:: Organic and biomolecular chemistry More from this journal
Volume:: 2
Issue:: 20
Pages:: 2988-2997
Publication date:: 2004-10-01
DOI:: 10.1039/b408255a
EISSN:: 1477-0539
ISSN:: 1477-0520

Language:: English
Keywords:: Molecular Structure

Hydrocarbons, Cyclic

Models, Chemical

Copper

Models, Molecular
Pubs id:: pubs:55231
UUID:: uuid:469f7b15-b499-42ed-9949-e1898aab5075
Local pid:: pubs:55231
Source identifiers:: 55231
Deposit date:: 2012-12-19

Terms of use

Copyright date:: 2004

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

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