| dc.contributor.author | Shinde, Anand H. | |
| dc.contributor.author | Dhokale, Ranjeet A. | |
| dc.contributor.author | Mague, Joel T. | |
| dc.contributor.author | Sathyamoorthi, Shyam | |
| dc.date.accessioned | 2023-06-13T20:03:10Z | |
| dc.date.available | 2023-06-13T20:03:10Z | |
| dc.date.issued | 2022-07-28 | |
| dc.identifier.citation | Shinde, A. H., Dhokale, R. A., Mague, J. T., & Sathyamoorthi, S. (2022). Highly Stereospecific Cyclizations of Homoallylic Silanols. The Journal of organic chemistry, 87(16), 11237–11252. https://doi.org/10.1021/acs.joc.2c01170 | en_US |
| dc.identifier.uri | https://hdl.handle.net/1808/34371 | |
| dc.description | This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, Copyright © 2022 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.2c01170. | en_US |
| dc.description.abstract | We demonstrate that di-tert-butylsilanols are competent nucleophiles for the intramolecular interception of palladium π-allyl species. In these reactions, allyl ethyl carbonates are the best precursors for the formation of palladium π-allyl intermediates, and [(Cinnamyl)PdCl]2/BINAP is superior to other Pd salt/ligand framework combinations. Our optimized protocol is compatible with a variety of silanol substrates. Importantly, the cyclization is perfectly stereospecific, proceeding via an anti-syn mechanism, which stands in contrast to reported analogous reactions of alcohols and phenols, known to proceed via an anti-anti mechanism. The alkenes in the product dioxasilinanes serve as blank slates for further functionalization. | en_US |
| dc.publisher | American Chemical Society | en_US |
| dc.rights | Copyright © 2022 American Chemical Society | en_US |
| dc.title | Highly Stereospecific Cyclizations of Homoallylic Silanols | en_US |
| dc.type | Article | en_US |
| kusw.kuauthor | Shinde, Anand H. | |
| kusw.kuauthor | Dhokale, Ranjeet A. | |
| kusw.kuauthor | Mague, Joel T. | |
| kusw.kuauthor | Sathyamoorthi, Shyam | |
| kusw.kudepartment | Medicinal Chemistry | en_US |
| dc.identifier.doi | 10.1021/acs.joc.2c01170 | en_US |
| dc.identifier.orcid | https://orcid.org/0000-0003-1966-8505 | en_US |
| dc.identifier.orcid | https://orcid.org/0000-0003-4705-7349 | en_US |
| kusw.oaversion | Scholarly/refereed, author accepted manuscript | en_US |
| kusw.oapolicy | This item meets KU Open Access policy criteria. | en_US |
| dc.identifier.pmid | PMC10019461 | en_US |
| dc.rights.accessrights | embargoedAccess | en_US |
