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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.
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).
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
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