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On the origins of diastereoselectivity in the alkylation of diketopiperazine enolates

Abstract:

High levels of diastereoselectivity are observed for benzylation of the lithium enolates of (S)-N,N′-bis-para-methoxybenzyl-3-iso-propyl- piperazine-2,5-dione, (S)-N(1)-para-methoxybenzyl-N(4)-methyl-3-iso-propyl- piperazine-2,5-dione and (S)-N(1)-methyl-N(4)-para-methoxybenzyl-3-iso-propyl- piperazine-2,5-dione. These data suggest that the high diastereofacial selectivity observed for alkylation of these diketopiperazine templates is mainly a consequence of the relay of stereochemical inform...

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Publication status:
Published

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Publisher copy:
10.1039/b701628j

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Garner, AC More by this author
Parkes, AL More by this author
Roberts, PM More by this author
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Journal:
NEW JOURNAL OF CHEMISTRY
Volume:
31
Issue:
4
Pages:
486-495
Publication date:
2007
DOI:
EISSN:
1369-9261
ISSN:
1144-0546
URN:
uuid:5c0f4257-6c4d-4d7a-948a-6488094d67d0
Source identifiers:
110570
Local pid:
pubs:110570
Language:
English

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