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Mechanism and applications of lithium amide-induced asymmetric rearrangements of 4-substituted and 4,4-disubstituted cyclopentene oxides to cyclopentenols

Abstract:

The preparation and lithium amide-induced rearrangements of 1,2-dideuterated 4-substituted cyclopentene oxides 11 and 19 are described, providing insight into the deprotonation mechanisms operating in such systems. Highly enantioselective syntheses of 4-substituted cis-4-hydroxymethylcyclopent-2-en-1-ols 32a-c are described. Also described are asymmetric syntheses of prostaglandin precursor 40 and (+)-iridomyrmecin (48) via highly enantioselective rearrangement of the epoxide 3 and subsequent...

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Publication status:
Published

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Publisher copy:
10.1039/a907522d

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:
24
Pages:
3579-3590
Publication date:
1999-01-01
DOI:
EISSN:
1364-5463
ISSN:
0300-922X
Language:
English
Pubs id:
pubs:37285
UUID:
uuid:e79a6556-1005-4a72-90a9-78244ca0af09
Local pid:
pubs:37285
Source identifiers:
37285
Deposit date:
2012-12-19

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