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Counterion-directed approach to the Diels-Alder paradigm: cascade synthesis of tricyclic fused cyclopropanes

Abstract:
An approach to the intramolecular Diels-Alder reaction has led to a cascade synthesis of complex carbocycles composed of three fused rings and up to five stereocentres with complete stereocontrol. Computational analysis reveals that the reaction proceeds via a Michael-Michael-cyclopropanation-epimerization cascade, in which size and coordination of the counterion is key.
Publication status:
Published
Peer review status:
Peer reviewed
Version:
Publisher's version

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Publisher copy:
10.1002/anie.201608534

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Department:
Oxford, MPLS, Chemistry
Role:
Author
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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Author
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Publisher:
Wiley-VCH Verlag Publisher's website
Journal:
Angewandte Chemie International Edition Journal website
Volume:
55
Issue:
44
Pages:
13813–13817
Publication date:
2016-01-01
Acceptance date:
2016-09-14
DOI:
EISSN:
1521-3757
ISSN:
0044-8249
Pubs id:
pubs:642725
URN:
uri:cb564e2a-46d1-42c4-9316-3c67ba453edc
UUID:
uuid:cb564e2a-46d1-42c4-9316-3c67ba453edc
Local pid:
pubs:642725
Paper number:
44

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