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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 s...

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Publisher copy:
10.1002/chem.201403255

Authors


Elbert, BL More by this author
Gudmundsson, HG More by this author
O'Hanlon, JA More by this author
Anderson, EA More by this author
Publisher:
Wiley-VCH Verlag
Journal:
Chemistry - A European Journal
Volume:
20
Issue:
28
Pages:
8594-8598
Publication date:
2014-07-07
DOI:
EISSN:
1521-3765
ISSN:
0947-6539
URN:
uuid:749cb773-3e3b-42db-b7a8-3155a78f7be6
Source identifiers:
476669
Local pid:
pubs:476669

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