Journal article

Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles.

Abstract:: A versatile nitro-Mannich/lactamisation cascade for the direct stereoselective synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles has been developed. A highly enantioenriched substituted 5-nitropiperidin-2-one was synthesised in a four component one-pot reaction combining an enantioselective organocatalytic Michael addition with the diastereoselective nitro-Mannich/lactamisation cascade. Protodenitration and chemoselective reductive manipulation of the heterocycles was used to install contiguous and fully substituted stereocentres in the synthesis of substituted piperidines.

Publication status:: Published

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APA Style

Jakubec, P., Cockfield, D., Helliwell, M., Raftery, J., & Dixon, D. (2012). Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles. Beilstein Journal of Organic Chemistry, 8, 567–578.

MLA Style

Jakubec, P., et al. “Stereoselective, Nitro-Mannich/Lactamisation Cascades for the Direct Synthesis of Heavily Decorated 5-Nitropiperidin-2-Ones and Related Heterocycles.” Beilstein Journal of Organic Chemistry, vol. 8, 2012, pp. 567–78.

Chicago Style

Jakubec, P, D Cockfield, M Helliwell, J Raftery, and D Dixon. 2012. “Stereoselective, Nitro-Mannich/Lactamisation Cascades for the Direct Synthesis of Heavily Decorated 5-Nitropiperidin-2-Ones and Related Heterocycles.” Beilstein Journal of Organic Chemistry 8: 567–78.
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Publisher copy:: 10.3762/bjoc.8.64

Authors

+ Jakubec, P More by this author

Role:: Author

+ Cockfield, D More by this author

Role:: Author

+ Helliwell, M More by this author

Role:: Author

+ Raftery, J More by this author

Role:: Author

+ Dixon, D More by this author

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

Journal:: Beilstein journal of organic chemistry More from this journal
Volume:: 8
Pages:: 567-578
Publication date:: 2012-01-01
DOI:: 10.3762/bjoc.8.64
EISSN:: 1860-5397
ISSN:: 1860-5397

Language:: English
Keywords:: imine

piperidine alkaloids

cascade

organocatalysis

nitro-Mannich

Michael addition
Pubs id:: pubs:325899
UUID:: uuid:532780ef-e275-4062-a574-8afd156d2d38
Local pid:: pubs:325899
Source identifiers:: 325899
Deposit date:: 2012-12-19

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Copyright date:: 2012

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

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