Journal article

Intramolecular hydride addition to pyridinium salts: new routes to enantiopure dihydropyridones.

Abstract:: The transformation of a simple disubstituted pyridine into a pyridinium ion bearing an exocyclic hydroxyl group, protected as a silane, enabled an intramolecular hydride transfer reaction to take place when fluoride was used as a nucleophile. The addition was both regio- and stereoselective and enabled the formation of enantiopure dihydropyridones when enantiopure pyridine derivatives were used in this sequence. The heterocyclic products contain ample functionality for further elaboration reactions and subsequent derivatization.

Publication status:: Published

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APA Style

Donohoe, T., Connolly, M., Rathi, A., & Walton, L. (2011). Intramolecular hydride addition to pyridinium salts: new routes to enantiopure dihydropyridones. Organic Letters, 13(8), 2074–2077.

MLA Style

Donohoe, T., et al. “Intramolecular Hydride Addition to Pyridinium Salts: New Routes to Enantiopure Dihydropyridones.” Organic Letters, vol. 13, no. 8, 2011, pp. 2074–77.

Chicago Style

Donohoe, T, M Connolly, A Rathi, and L Walton. 2011. “Intramolecular Hydride Addition to Pyridinium Salts: New Routes to Enantiopure Dihydropyridones.” Organic Letters 13 (8): 2074–77.
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Publisher copy:: 10.1021/ol200478p

Authors

+ Donohoe, T More by this author

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

+ Connolly, M More by this author

Role:: Author

+ Rathi, A More by this author

Role:: Author

+ Walton, L More by this author

Role:: Author

Journal:: Organic letters More from this journal
Volume:: 13
Issue:: 8
Pages:: 2074-2077
Publication date:: 2011-04-01
DOI:: 10.1021/ol200478p
EISSN:: 1523-7052
ISSN:: 1523-7060

Language:: English
Keywords:: Hydrogenation

Molecular Structure

Pyridones

Pyridinium Compounds

Stereoisomerism

Models, Molecular
Pubs id:: pubs:127160
UUID:: uuid:c1c4bf57-c61f-4379-909d-8bbb84f73587
Local pid:: pubs:127160
Source identifiers:: 127160
Deposit date:: 2012-12-19

Terms of use

Copyright date:: 2011

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

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