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Functionalised bicyclic alcohols by enantioselective alpha-deprotonation-rearrangement of meso-epoxides

Abstract:
Enantioselective α-deprotonation-rearrangement of achiral substituted cyclooctene oxides 7, 27 and 28 and N-Boc hexahydroazonine oxide 45 using organolithiums in the presence of (-)-sparteine 3 or (-)-α-isosparteine 4 gives the functionalised bicyclo[3.3.0]octan-2-ols 9, 29, and 32 and indolizinol 47 in 50-72% yields and 83-89% ees.
Publication status:
Published

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Publisher copy:
10.1039/b105369h

Authors


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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 More from this journal
Issue:
18
Pages:
2161-2174
Publication date:
2001-09-21
DOI:
EISSN:
1364-5463
ISSN:
1472-7781
Language:
English
Pubs id:
pubs:37989
UUID:
uuid:ab2698f1-910d-409c-9aad-8c00bdf0ed62
Local pid:
pubs:37989
Source identifiers:
37989
Deposit date:
2012-12-19

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