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Isomerisations of cycloalkene- and bicycloalkene-derived achiral epoxides by enantioselective alpha-deprotonation

Abstract:

Enantioselective α-deprotonation-rearrangement of cis-cyclooctene oxide 1 using organolithiums in the presence of (-)-sparteine 4 or (-)-α-isosparteine 5 gives the (-)-alcohol 2 in good yields and ees. The use of C2-symmetric bisoxazolines (-)-6a-d as ligands allows access to the (+)-alcohol 2. (-)-α-Isosparteine 5 functions as an efficient asymmetric ligand catalyst in the rearrangement of 1. The α-deprotonation process can be extended to other cycloalkene-derived achiral epoxides 7, 9, 11, ...

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Publication status:
Published

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Publisher copy:
10.1039/a802434k

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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:
14
Pages:
2151-2161
Publication date:
1998-07-21
DOI:
EISSN:
1364-5463
ISSN:
0300-922X
Language:
English
Pubs id:
pubs:36645
UUID:
uuid:05b9d01a-8ce8-494a-b264-caa4203a1527
Local pid:
pubs:36645
Source identifiers:
36645
Deposit date:
2012-12-19

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