Lead-Mediated Highly Diastereoselective Allylation of Aldehydes with Cyclic Allylic Halides

Bu Qing Cheng; Shi Wen Zhao; Xuan DI Song; Xue Qiang Chu; Weidong Rao; Teck Peng Loh; Zhi Liang Shen

doi:10.1021/acs.joc.9b00370

Lead-Mediated Highly Diastereoselective Allylation of Aldehydes with Cyclic Allylic Halides

Bu Qing Cheng, Shi Wen Zhao, Xuan DI Song, Xue Qiang Chu, Weidong Rao, Teck Peng Loh, Zhi Liang Shen

School of Chemistry and Moleculai Engineering

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

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).

Original language	English
Pages (from-to)	5348-5356
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	84
Issue number	9
DOIs	https://doi.org/10.1021/acs.joc.9b00370
State	Published - 3 May 2019

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title = "Lead-Mediated Highly Diastereoselective Allylation of Aldehydes with Cyclic Allylic Halides",

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).",

author = "Cheng, {Bu Qing} and Zhao, {Shi Wen} and Song, {Xuan DI} and Chu, {Xue Qiang} and Weidong Rao and Loh, {Teck Peng} and Shen, {Zhi Liang}",

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doi = "10.1021/acs.joc.9b00370",

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T1 - Lead-Mediated Highly Diastereoselective Allylation of Aldehydes with Cyclic Allylic Halides

AU - Cheng, Bu Qing

AU - Zhao, Shi Wen

AU - Song, Xuan DI

AU - Chu, Xue Qiang

AU - Rao, Weidong

AU - Loh, Teck Peng

AU - Shen, Zhi Liang

PY - 2019/5/3

Y1 - 2019/5/3

N2 - 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).

AB - 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).

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DO - 10.1021/acs.joc.9b00370

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SN - 0022-3263

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EP - 5356

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 9

ER -

Lead-Mediated Highly Diastereoselective Allylation of Aldehydes with Cyclic Allylic Halides

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