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https://hdl.handle.net/10356/147494
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DC Field | Value | Language |
---|---|---|
dc.contributor.author | Cheng, Bu-Qing | en_US |
dc.contributor.author | Zhao, Shi-Wen | en_US |
dc.contributor.author | Song, Xuan-Di | en_US |
dc.contributor.author | Chu, Xue-Qiang | en_US |
dc.contributor.author | Rao, Weidong | en_US |
dc.contributor.author | Loh, Teck-Peng | en_US |
dc.contributor.author | Shen, Zhi-Liang | en_US |
dc.date.accessioned | 2021-04-05T02:06:05Z | - |
dc.date.available | 2021-04-05T02:06:05Z | - |
dc.date.issued | 2019 | - |
dc.identifier.citation | Cheng, B., Zhao, S., Song, X., Chu, X., Rao, W., Loh, T. & Shen, Z. (2019). Lead-mediated highly diastereoselective allylation of aldehydes with cyclic allylic halides. The Journal of Organic Chemistry, 84(9), 5348-5356. https://dx.doi.org/10.1021/acs.joc.9b00370 | en_US |
dc.identifier.issn | 0022-3263 | en_US |
dc.identifier.uri | https://hdl.handle.net/10356/147494 | - |
dc.description.abstract | Lead was found to efficiently mediate the allylation reactions of carbonyl compounds with cyclic allylic halides in the presence of stoichiometric amounts of lithium chloride and a catalytic amount of GaCl3 (20 mol %), leading to the desired homoallylic alcohols in modest to high yields with excellent diastereocontrol (>99:1 syn/anti) and good functional group tolerance. In contrast, the use of either 2-pyridinecarboxaldehyde as the carbonyl substrate or ( E)-cinnamyl bromide as the allylating agent produced the corresponding product with reversed diastereoselectivity (>99:1 anti/syn). | en_US |
dc.description.sponsorship | Nanyang Technological University | en_US |
dc.language.iso | en | en_US |
dc.relation.ispartof | The Journal of Organic Chemistry | en_US |
dc.rights | © 2019 American Chemical Society. All rights reserved. | en_US |
dc.subject | Science::Chemistry | en_US |
dc.title | Lead-mediated highly diastereoselective allylation of aldehydes with cyclic allylic halides | en_US |
dc.type | Journal Article | en |
dc.contributor.school | School of Physical and Mathematical Sciences | en_US |
dc.identifier.doi | 10.1021/acs.joc.9b00370 | - |
dc.identifier.pmid | 30977647 | - |
dc.identifier.scopus | 2-s2.0-85065170853 | - |
dc.identifier.issue | 9 | en_US |
dc.identifier.volume | 84 | en_US |
dc.identifier.spage | 5348 | en_US |
dc.identifier.epage | 5356 | en_US |
dc.subject.keywords | Donor-acceptor Cyclopropanes | en_US |
dc.subject.keywords | Aqueous-media | en_US |
dc.description.acknowledgement | We gratefully acknowledge the financial support from Nanjing Tech University (Start-up grant nos. 39837118, 39837101, and 39837146), the SICAM Fellowship from Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Forestry University, and Nanyang Technological University. | en_US |
item.fulltext | No Fulltext | - |
item.grantfulltext | none | - |
Appears in Collections: | SPMS Journal Articles |
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