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Atropisomeric amides as chiral ligands: using (-)-sparteine-directed enantioselective silylation to control the conformation of a stereogenic axis

Abstract:

An enantiomerically pure (1-trimethylsilyl)ethyl group, constructed by a (-)-sparteine-directed enantioselective quench of a laterally lithiated tertiary aromatic amide, exerts powerful thermodynamic control over the conformation of the adjacent tertiary amide substituent. Ortholithiation and functionalization of the amide in the 6-position allows the single amide conformer to be trapped as an enantiomerically and diastereoisomerically pure amide atropisomer. Protodesilylation of the amide gi...

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Publication status:
Published

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Publisher copy:
10.1021/jo0007074

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Institution:
University of Oxford
Division:
MSD
Department:
Surgical Sciences
Role:
Author
Journal:
Journal of organic chemistry
Volume:
65
Issue:
21
Pages:
7033-7040
Publication date:
2000-10-01
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
Source identifiers:
244883
Language:
English
Pubs id:
pubs:244883
UUID:
uuid:2b0a1e96-e948-4f8a-8e8b-83edfd2ac442
Local pid:
pubs:244883
Deposit date:
2012-12-19

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