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Journal article

N-acyl 'quat' pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis

Abstract:
A novel route to chiral amides through the efficient, non-racemising, cleavage of N-acyl side chains from a 'Quat' chiral auxiliary using N-centred nucleophiles is described. The synthetic utility of the procedure is then highlighted by the preparation of a range of succinamide and succinimide derivatives and through the synthesis of the natural product (S)-(+)-amphetamine via a stereospecific Hofman type degradation using a hypervalent iodine reagent.
Publication status:
Published

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Publisher copy:
10.1039/b205326h

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 More from this journal
Issue:
16
Pages:
1869-1876
Publication date:
2002-08-21
DOI:
EISSN:
1364-5463
ISSN:
1472-7781
Language:
English
Pubs id:
pubs:38339
UUID:
uuid:aaf39900-b09d-4b0c-a8a3-c7edf17b8763
Local pid:
pubs:38339
Source identifiers:
38339
Deposit date:
2012-12-19

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