Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/147432
Title: Bismuth-mediated diastereoselective allylation reaction of carbonyl compounds with cyclic allylic halides or cinnamyl halide
Authors: Liu, Xuan-Yu
Cheng, Bu-Qing
Guo, Yi-Cong
Chu, Xue-Qiang
Li, Yongxin
Loh, Teck-Peng
Shen, Zhi-Liang
Keywords: Science::Chemistry
Issue Date: 2019
Source: Liu, X., Cheng, B., Guo, Y., Chu, X., Li, Y., Loh, T. & Shen, Z. (2019). Bismuth-mediated diastereoselective allylation reaction of carbonyl compounds with cyclic allylic halides or cinnamyl halide. Advanced Synthesis & Catalysis, 361(3), 542-549. https://dx.doi.org/10.1002/adsc.201801297
Journal: Advanced Synthesis & Catalysis
Abstract: An efficient diastereoselective allylation of various carbonyl compounds with cyclic allylic halides by using commercially available bismuth powder in the presence of LiI was developed. Among all the metals screened, bismuth was found to be the best mediator for the transformation. The reactions involving various cyclic allylic halides proceeded smoothly at room temperature to produce the desired homoallylic alcohols in good to excellent yields with high diastereoselectivities (>99:1 dr). Reversed diastereoselectivity was obtained when carbonyl substrate (e. g., 2-pyridinecarboxaldehyde, glyoxylic acid) containing chelating substituent was used in the allylation reaction. In addition, the reactions involving acyclic (E)-cinnamyl bromide as substrate worked equally well with high diastereocontrol. (Figure presented.).
URI: https://hdl.handle.net/10356/147432
ISSN: 1615-4150
DOI: 10.1002/adsc.201801297
Rights: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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