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Synthesis of cyclic alkenylsiloxanes by semihydrogenation: a stereospecific route to (Z)-alkenyl polyenes.

Abstract:
Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes-a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama-Denmark coupling to give (Z)-alkenyl polyene motifs found in bioactive natural products. The ring size of the silane is crucial: five-membered cyclic siloxanes also couple under fluoride-free conditions, whilst their six-membered homologues do not, enabling orthogonality within this structural motif.
Publication status:
Published

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Publisher copy:
10.1002/chem.201403255

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
Chemistry (Weinheim an der Bergstrasse, Germany) More from this journal
Volume:
20
Issue:
28
Pages:
8594-8598
Publication date:
2014-07-01
DOI:
EISSN:
1521-3765
ISSN:
0947-6539
Language:
English
Keywords:
Pubs id:
pubs:469552
UUID:
uuid:f5fa7aaa-a2b9-459a-86ee-0a2860d7e9a9
Local pid:
pubs:469552
Source identifiers:
469552
Deposit date:
2014-06-20

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