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- Publisher Website: 10.1055/s-0037-1611537
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Article: Triphenylphosphine Oxide-Catalyzed Selective α,β-Reduction of Conjugated Polyunsaturated Ketones
Title | Triphenylphosphine Oxide-Catalyzed Selective α,β-Reduction of Conjugated Polyunsaturated Ketones |
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Authors | |
Keywords | triphenylphosphine oxide trichlorosilane reduction Lewis base organocatalysis |
Issue Date | 2019 |
Publisher | Thieme Publishing. The Journal's web site is located at http://www.thieme-chemistry.com/thieme-chemistry/journals/info/synlett/index.shtml |
Citation | Synlett, 2019, v. 30 n. 9, p. 1100-1104 How to Cite? |
Abstract | The scope of the triphenylphosphine oxide-catalyzed reduction of conjugated polyunsaturated ketones using trichlorosilane as the reducing reagent has been examined. In all cases studied, the α,β-C=C double bond was selectively reduced to a C–C single bond while all other reducible functional groups remained unchanged. This reaction was applied to a large variety of conjugated dienones, a trienone, and a tetraenone. Additionally, a tandem one-pot Wittig/conjugate-reduction reaction sequence was developed to produce γ,δ-unsaturated ketones directly from simple building blocks. In these reactions the byproduct of the Wittig reaction served as the catalyst for the reduction reaction. This strategy was then used in the synthesis of naturally occurring moth pheromones to demonstrate its utility in the context of natural-product synthesis. |
Persistent Identifier | http://hdl.handle.net/10722/273376 |
ISSN | 2023 Impact Factor: 1.7 2023 SCImago Journal Rankings: 0.450 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Xia, X | - |
dc.contributor.author | LAO, Z | - |
dc.contributor.author | Toy, PH | - |
dc.date.accessioned | 2019-08-06T09:27:45Z | - |
dc.date.available | 2019-08-06T09:27:45Z | - |
dc.date.issued | 2019 | - |
dc.identifier.citation | Synlett, 2019, v. 30 n. 9, p. 1100-1104 | - |
dc.identifier.issn | 0936-5214 | - |
dc.identifier.uri | http://hdl.handle.net/10722/273376 | - |
dc.description.abstract | The scope of the triphenylphosphine oxide-catalyzed reduction of conjugated polyunsaturated ketones using trichlorosilane as the reducing reagent has been examined. In all cases studied, the α,β-C=C double bond was selectively reduced to a C–C single bond while all other reducible functional groups remained unchanged. This reaction was applied to a large variety of conjugated dienones, a trienone, and a tetraenone. Additionally, a tandem one-pot Wittig/conjugate-reduction reaction sequence was developed to produce γ,δ-unsaturated ketones directly from simple building blocks. In these reactions the byproduct of the Wittig reaction served as the catalyst for the reduction reaction. This strategy was then used in the synthesis of naturally occurring moth pheromones to demonstrate its utility in the context of natural-product synthesis. | - |
dc.language | eng | - |
dc.publisher | Thieme Publishing. The Journal's web site is located at http://www.thieme-chemistry.com/thieme-chemistry/journals/info/synlett/index.shtml | - |
dc.relation.ispartof | Synlett | - |
dc.rights | Synlett. Copyright © Thieme Publishing. | - |
dc.subject | triphenylphosphine oxide | - |
dc.subject | trichlorosilane | - |
dc.subject | reduction | - |
dc.subject | Lewis base | - |
dc.subject | organocatalysis | - |
dc.title | Triphenylphosphine Oxide-Catalyzed Selective α,β-Reduction of Conjugated Polyunsaturated Ketones | - |
dc.type | Article | - |
dc.identifier.email | Toy, PH: phtoy@hkucc.hku.hk | - |
dc.identifier.authority | Toy, PH=rp00791 | - |
dc.description.nature | postprint | - |
dc.identifier.doi | 10.1055/s-0037-1611537 | - |
dc.identifier.scopus | eid_2-s2.0-85065867808 | - |
dc.identifier.hkuros | 300764 | - |
dc.identifier.volume | 30 | - |
dc.identifier.issue | 9 | - |
dc.identifier.spage | 1100 | - |
dc.identifier.epage | 1104 | - |
dc.identifier.isi | WOS:000469034000018 | - |
dc.publisher.place | Germany | - |
dc.identifier.issnl | 0936-5214 | - |