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

Bryony L. Elbert; Diane S.W. Lim; Haraldur G. Gudmundsson; Jack A. O'Hanlon; Edward A. Anderson

doi:10.1002/chem.201403255

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

Bryony L. Elbert, Diane S.W. Lim, Haraldur G. Gudmundsson, Jack A. O'Hanlon, Edward A. Anderson^*

^*Corresponding author for this work

Faculty of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

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.

Original language	English
Pages (from-to)	8594-8598
Number of pages	5
Journal	Chemistry - A European Journal
Volume	20
Issue number	28
DOIs	https://doi.org/10.1002/chem.201403255
Publication status	Published - 7 Jul 2014

Other keywords

alkynes
cross-coupling
hydrogenation
natural products
silanes

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title = "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.",

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T2 - A stereospecific route to (Z)-alkenyl polyenes

AU - Elbert, Bryony L.

AU - Lim, Diane S.W.

AU - Gudmundsson, Haraldur G.

AU - O'Hanlon, Jack A.

AU - Anderson, Edward A.

PY - 2014/7/7

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AB - 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.

KW - alkynes

KW - cross-coupling

KW - hydrogenation

KW - natural products

KW - silanes

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JF - Chemistry - A European Journal

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ER -

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

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