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Conjugate additions of organocuprates to a 3-methylene-6-isopropyldiketopiperazine acceptor for the asymmetric synthesis of homochiral alpha-amino acids

Abstract:
Addition of a range of organocuprates to (S)-N,N′-bis(p-methoxybenzyl)-3-methylene-6-isopropylpiperazine-2, 5-dione 8 affords cis-3-isopropyl-6-alkyldiketopiperazines in excellent yield and >95% de. Subsequent deprotection and hydrolysis of these cis-3-isopropyl-6-alkyldiketopiperazines affords homochiral (S)-α-amino acids in excellent yield.
Publication status:
Published

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Publisher copy:
10.1039/b108621a

Authors


More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Garner, AC More by this author
O'Shea, MD More by this author
Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Issue:
24
Pages:
3281-3287
Publication date:
2001
DOI:
EISSN:
1364-5463
ISSN:
1472-7781
URN:
uuid:ca141bd0-4fd9-49ea-87fe-aa959fb34db7
Source identifiers:
110594
Local pid:
pubs:110594
Language:
English

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