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https://hdl.handle.net/10356/147494
Title: | Lead-mediated highly diastereoselective allylation of aldehydes with cyclic allylic halides | Authors: | Cheng, Bu-Qing Zhao, Shi-Wen Song, Xuan-Di Chu, Xue-Qiang Rao, Weidong Loh, Teck-Peng Shen, Zhi-Liang |
Keywords: | Science::Chemistry | Issue Date: | 2019 | Source: | 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 | Journal: | The Journal of Organic Chemistry | 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). | URI: | https://hdl.handle.net/10356/147494 | ISSN: | 0022-3263 | DOI: | 10.1021/acs.joc.9b00370 | Schools: | School of Physical and Mathematical Sciences | Rights: | © 2019 American Chemical Society. All rights reserved. | Fulltext Permission: | none | Fulltext Availability: | No Fulltext |
Appears in Collections: | SPMS Journal Articles |
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