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铑催化碳酸乙烯基亚乙酯与亚硝基苯亚胺的串联不对称烯丙基脱羧加成和环化反应

Rhodium-Catalyzed Tandem Asymmetric Allylic Decarboxylative Addition and Cyclization of Vinylethylene Carbonates with -Nosylimines.

作者信息

Wang Xiao-Lin, Jiang Hai-Bin, Zheng Sheng-Cai, Zhao Xiao-Ming

机构信息

School of Chemical Science and Engineering, Tongji University, 1239 Siping Road, Shanghai 200092, China.

出版信息

Molecules. 2024 Feb 26;29(5):1019. doi: 10.3390/molecules29051019.

Abstract

A enantioselective tandem transformation, concerning asymmetric allylic decarboxylative addition and cyclization of -nosylimines with vinylethylene carbonates (VECs), in the presence of [Rh(CH)Cl], chiral sulfoxide--olefin tridentate ligand has been developed. The reaction of VECs with various substituted -nosylimines proceeded smoothly under mild conditions, providing highly functionalized oxazolidine frameworks in good to high yields with good to excellent enantioselectivity.

摘要

已开发出一种对映选择性串联转化反应,该反应涉及在[Rh(CH)Cl]和手性亚砜-烯烃三齿配体存在下,-亚磺酰亚胺与碳酸乙烯亚乙酯(VECs)的不对称烯丙基脱羧加成和环化反应。VECs与各种取代的-亚磺酰亚胺的反应在温和条件下顺利进行,以良好至高产率和良好至优异的对映选择性提供了高度官能化的恶唑烷骨架。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0fdd/10934018/cab7ca8d5cae/molecules-29-01019-sch001.jpg

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本文引用的文献

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Tridentate Sulfoxide--olefin Hybrid Ligands in Rhodium-Catalyzed Asymmetric Allylic Substitution.
Org Lett. 2024 Mar 8;26(9):1970-1974. doi: 10.1021/acs.orglett.4c00487. Epub 2024 Feb 29.
3
Rh-Catalyzed Regio- and Enantioselective Allylic Phosphinylation.
J Am Chem Soc. 2022 Feb 23;144(7):2893-2898. doi: 10.1021/jacs.2c00239. Epub 2022 Feb 14.
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Stereodivergent Synthesis of Enantioenriched γ-Butyrolactones Bearing Two Vicinal Stereocenters Enabled by Synergistic Copper and Iridium Catalysis.
Angew Chem Int Ed Engl. 2021 Nov 15;60(47):24930-24940. doi: 10.1002/anie.202107418. Epub 2021 Oct 20.
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Rhodium-Catalyzed Regio- and Enantioselective Allylic Amination of Racemic 1,2-Disubstituted Allylic Phosphates.
J Am Chem Soc. 2021 Jun 9;143(22):8255-8260. doi: 10.1021/jacs.1c04016. Epub 2021 May 24.
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Enantioselective Synthesis of 3-Allylindolizines via Sequential Rh-Catalyzed Asymmetric Allylation and Tschitschibabin Reaction.
Org Lett. 2020 Dec 18;22(24):9456-9461. doi: 10.1021/acs.orglett.0c03383. Epub 2020 Dec 2.
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Vinylethylene Carbonates as -Unsaturated Aldehyde Surrogates for Regioselective [3 + 3] Cycloaddition.
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