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Synthesis of medium-ring lactones via tandem methylenation/Claisen rearrangement of cyclic carbonates

Abstract:

The conversion of vinyl-substituted 6- and 7-membered cyclic carbonates into 8- and 9-membered medium-ring lactones has been achieved in good yield using dimethyltitanocene in toluene at reflux. The reaction proceeds by initial formation of a ketene acetal which undergoes subsequent in situ Claisen rearrangement to provide the corresponding lactones. The preparation of the cyclic carbonates is carried out under basic conditions and hence this methodology complements our existing selenium-base...

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Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Journal:
TETRAHEDRON
Volume:
58
Issue:
10
Pages:
1943-1971
Publication date:
2002-03-04
DOI:
ISSN:
0040-4020
URN:
uuid:72298cd1-1bd7-4507-a226-776c7c958dcc
Source identifiers:
58703
Local pid:
pubs:58703

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