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Chiral glycine cation equivalents: N-acyliminium species derived from diketopiperazines

Abstract:

Studies towards a N,N′-bis(p-methoxybenzyl)diketopiperazine asymmetric glycine cation equivalent for the synthesis of homochiral α-amino acids are described. The oxidation of enolate 3 with molecular oxygen provides either a mixture of hydroxylated diketopiperazines 7 and 8 or trione 10 depending upon the reaction conditions. The nucleophilic reduction of trione 10 and the reaction of acetoxy N-acyliminium ion precursors 5 and 6, derived from 7 and 8, with allyltrimethylsilane and boron trifl...

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Publication status:
Published

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Publisher copy:
10.1039/b207457p

Authors


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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:
22
Pages:
2442-2448
Publication date:
2002-01-01
DOI:
EISSN:
1364-5463
ISSN:
1472-7781
Language:
English
Pubs id:
pubs:110585
UUID:
uuid:29852d39-6a74-4f00-848d-51acc5782c98
Local pid:
pubs:110585
Source identifiers:
110585
Deposit date:
2012-12-19

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