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- Publisher Website: 10.1002/anie.201900693
- Scopus: eid_2-s2.0-85064005621
- PMID: 30946506
- WOS: WOS:000471976400046
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Article: Catalytic (3+2) Palladium-Aminoallyl Cycloaddition with Conjugated Dienes
Title | Catalytic (3+2) Palladium-Aminoallyl Cycloaddition with Conjugated Dienes |
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Authors | |
Keywords | (3+2) cycloaddition aminoallyl dienes palladium pyrrolidines |
Issue Date | 2019 |
Citation | Angewandte Chemie - International Edition, 2019, v. 58, n. 19, p. 6396-6399 How to Cite? |
Abstract | © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim We describe the design and application of tailored aminoallyl precursors for catalytic (3+2) cycloaddition with conjugated dienes via a Pd-aminoallyl intermediate. The new cycloaddition reactions override the conventional (4+3) selectivity of aminoallyl cation cycloaddition through a sequence of Pd-allyl transfer and ring closure. A variety of highly substituted or fused pyrrolidine rings were synthesized using the cycloaddition, and can further undergo [1,3] N-to-C rearrangement to five-membered carbocycles with a different palladium catalyst. The utility of the (3+2) cycloaddition is also demonstrated by the preparation of various derivatives from the bicyclic pyrrolidine products. |
Persistent Identifier | http://hdl.handle.net/10722/276641 |
ISSN | 2023 Impact Factor: 16.1 2023 SCImago Journal Rankings: 5.300 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Trost, Barry M. | - |
dc.contributor.author | Huang, Zhongxing | - |
dc.date.accessioned | 2019-09-18T08:34:13Z | - |
dc.date.available | 2019-09-18T08:34:13Z | - |
dc.date.issued | 2019 | - |
dc.identifier.citation | Angewandte Chemie - International Edition, 2019, v. 58, n. 19, p. 6396-6399 | - |
dc.identifier.issn | 1433-7851 | - |
dc.identifier.uri | http://hdl.handle.net/10722/276641 | - |
dc.description.abstract | © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim We describe the design and application of tailored aminoallyl precursors for catalytic (3+2) cycloaddition with conjugated dienes via a Pd-aminoallyl intermediate. The new cycloaddition reactions override the conventional (4+3) selectivity of aminoallyl cation cycloaddition through a sequence of Pd-allyl transfer and ring closure. A variety of highly substituted or fused pyrrolidine rings were synthesized using the cycloaddition, and can further undergo [1,3] N-to-C rearrangement to five-membered carbocycles with a different palladium catalyst. The utility of the (3+2) cycloaddition is also demonstrated by the preparation of various derivatives from the bicyclic pyrrolidine products. | - |
dc.language | eng | - |
dc.relation.ispartof | Angewandte Chemie - International Edition | - |
dc.subject | (3+2) cycloaddition | - |
dc.subject | aminoallyl | - |
dc.subject | dienes | - |
dc.subject | palladium | - |
dc.subject | pyrrolidines | - |
dc.title | Catalytic (3+2) Palladium-Aminoallyl Cycloaddition with Conjugated Dienes | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1002/anie.201900693 | - |
dc.identifier.pmid | 30946506 | - |
dc.identifier.scopus | eid_2-s2.0-85064005621 | - |
dc.identifier.volume | 58 | - |
dc.identifier.issue | 19 | - |
dc.identifier.spage | 6396 | - |
dc.identifier.epage | 6399 | - |
dc.identifier.eissn | 1521-3773 | - |
dc.identifier.isi | WOS:000471976400046 | - |
dc.identifier.issnl | 1433-7851 | - |