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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 heterocycle...

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Publication status:
Published

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Publisher copy:
10.3762/bjoc.8.64

Authors


Jakubec, P More by this author
Cockfield, DM More by this author
Helliwell, M More by this author
Raftery, J More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
Beilstein journal of organic chemistry
Volume:
8
Pages:
567-578
Publication date:
2012
DOI:
EISSN:
1860-5397
ISSN:
1860-5397
URN:
uuid:532780ef-e275-4062-a574-8afd156d2d38
Source identifiers:
325899
Local pid:
pubs:325899

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