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Journal article

2-Halo-diketopiperazines as chiral glycine cation equivalents

Abstract:

A range of (2S,5S)-5-isopropyl-2-halo-N,N′-bis-(p-methoxybenzyl)- piperazine-3,6-diones 8 (Cl), 11, 12 (F) and 13 (Br) have been prepared, either via electrophilic halogenation of the corresponding lithiated diketopiperazine, or via transhalogenation from fluoro-11 and 12. The product distribution and stereoselectivity of additions of allyltrimethylsilane, sodium thiophenolate and a range of organomagnesium reagents to chloro 8 are reported. In the reactions with Grignard reagents the observe...

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Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Garner, AC More by this author
Savory, ED More by this author
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Journal:
TETRAHEDRON-ASYMMETRY
Volume:
15
Issue:
24
Pages:
3989-4001
Publication date:
2004-12-13
DOI:
ISSN:
0957-4166
URN:
uuid:2419d1f6-ee57-4779-aa1e-682db0422925
Source identifiers:
110574
Local pid:
pubs:110574
Language:
English

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