Journal article

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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APA Style

Elbert, B., Lim, D., Gudmundsson, H., O'Hanlon, J., & Anderson, E. (2014). Synthesis of cyclic alkenylsiloxanes by semihydrogenation: a stereospecific route to (Z)-alkenyl polyenes. Chemistry (Weinheim an Der Bergstrasse, Germany), 20(28), 8594–8598.

MLA Style

Elbert, B, et al. “Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: a Stereospecific Route to (Z)-Alkenyl Polyenes.” Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 20, no. 28, 2014, pp. 8594–98.

Chicago Style

Elbert, B, D Lim, H Gudmundsson, J O'Hanlon, and E Anderson. 2014. “Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: a Stereospecific Route to (Z)-Alkenyl Polyenes.” Chemistry (Weinheim an Der Bergstrasse, Germany) 20 (28): 8594–98.
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Publisher copy:: 10.1002/chem.201403255

Authors

+ Elbert, B More by this author

Role:: Author

+ Lim, D More by this author

Role:: Author

+ Gudmundsson, H More by this author

Role:: Author

+ O'Hanlon, J More by this author

Role:: Author

+ Anderson, E More by this author

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:: 10.1002/chem.201403255
EISSN:: 1521-3765
ISSN:: 0947-6539

Language:: English
Keywords:: alkynes

hydrogenation

silanes

cross-coupling

natural products
Pubs id:: pubs:469552
UUID:: uuid:f5fa7aaa-a2b9-459a-86ee-0a2860d7e9a9
Local pid:: pubs:469552
Source identifiers:: 469552
Deposit date:: 2014-06-20
ARK identifier:: ark:/29072/ora_f5fa7aaaa2b9459a86ee0a2860d7e9a9

Terms of use

Copyright date:: 2014

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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