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Catalytic enantioselective Michael additions to unsaturated ester derivatives using chiral copper(II) Lewis acid complexes.

Abstract:
[formula: see text] Chiral Cu(II) bisoxazoline (box) Lewis acids have been developed as catalysts of the Michael addition of enolsilanes to unsaturated ester derivatives. While enantioselection is stereoregular, the sense of diastereoselection is directly related to thioester enolsilane geometry: (E) enolsilanes give anti adducts and (Z) enolsilanes afford syn adducts. The size of the enolsilane alkylthio substituent directly impacts the magnitude of diastereoselection.
Publication status:
Published

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Publisher copy:
10.1021/ol9901570

Authors


Willis, MC More by this author
Johnston, JN More by this author
Journal:
Organic letters
Volume:
1
Issue:
6
Pages:
865-868
Publication date:
1999-09-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:f1d8aa6e-e99e-4eb0-912d-57cf37075990
Source identifiers:
52455
Local pid:
pubs:52455
Language:
English
Keywords:

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