铑（I）催化的炔烃与联烯基环丙烷的分子内[5+2]环加成反应：双环[5.4.0]十一碳三烯和双环[5.5.0]十二碳三烯的构建 - Suppr

Rhodium(I)-catalyzed intramolecular [5+2] cycloaddition reactions of alkynes and allenylcyclopropanes: construction of bicyclo[5.4.0]undecatrienes and bicyclo[5.5.0]dodecatrienes.

作者信息

Inagaki Fuyuhiko, Sugikubo Katsuya, Miyashita Yusuke, Mukai Chisato

机构信息

Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.

出版信息

Angew Chem Int Ed Engl. 2010 Mar 15;49(12):2206-10. doi: 10.1002/anie.200906994.

DOI:10.1002/anie.200906994

PMID:20175176

Abstract

摘要

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Rhodium(I)-catalyzed intramolecular [5+2] cycloaddition reactions of alkynes and allenylcyclopropanes: construction of bicyclo[5.4.0]undecatrienes and bicyclo[5.5.0]dodecatrienes.

作者信息

Inagaki Fuyuhiko, Sugikubo Katsuya, Miyashita Yusuke, Mukai Chisato

机构信息

Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.

出版信息

Angew Chem Int Ed Engl. 2010 Mar 15;49(12):2206-10. doi: 10.1002/anie.200906994.

DOI:10.1002/anie.200906994

PMID:20175176

Abstract

摘要

相似文献

Rhodium(I)-catalyzed intramolecular [5+2] cycloaddition reactions of alkynes and allenylcyclopropanes: construction of bicyclo[5.4.0]undecatrienes and bicyclo[5.5.0]dodecatrienes.

Angew Chem Int Ed Engl. 2010 Mar 15;49(12):2206-10. doi: 10.1002/anie.200906994.

Stereospecific and stereoselective rhodium(I)-catalyzed intramolecular [2+2+2] cycloaddition of allene-ene-ynes: construction of bicyclo[4.1.0]heptenes.

Angew Chem Int Ed Engl. 2015 Jan 19;54(4):1240-4. doi: 10.1002/anie.201409155. Epub 2014 Oct 29.

Intermolecular rhodium-catalyzed [3+2+2] carbocyclization of alkenylidenecyclopropanes with activated alkynes: regio- and diastereoselective construction of cis-fused bicycloheptadienes.

J Am Chem Soc. 2008 Oct 1;130(39):12838-9. doi: 10.1021/ja803691p. Epub 2008 Sep 9.

Rhodium-catalyzed 1,3-acyloxy migration and subsequent intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne.

Chem Commun (Camb). 2012 Feb 21;48(16):2204-6. doi: 10.1039/c2cc17406e. Epub 2012 Jan 17.

Rhodium(I)-catalyzed intramolecular carbonylative [2+2+1] cycloaddition of bis(allene)s: bicyclo[6.3.0]undecadienones and bicyclo[5.3.0]decadienones.

Angew Chem Int Ed Engl. 2009;48(11):2007-11. doi: 10.1002/anie.200806029.

Construction of Azabicyclo[6.4.0]dodecatrienes Based on Rhodium(I)-Catalyzed Intramolecular [6+2] Cycloaddition between Azetidine, Allene, and Alkynes.

Chem Pharm Bull (Tokyo). 2016;64(7):805-10. doi: 10.1248/cpb.c16-00178.

Rh(I)-catalyzed [6+2] cycloaddition of alkyne-allenylcyclobutanes: a new entry for the synthesis of bicyclo[6.m.0] skeletons.

Chemistry. 2011 Aug 8;17(33):9062-5. doi: 10.1002/chem.201101441. Epub 2011 Jul 15.

Origins of differences in reactivities of alkenes, alkynes, and allenes in [Rh(CO)2Cl]2-catalyzed (5 + 2) cycloaddition reactions with vinylcyclopropanes.

J Am Chem Soc. 2008 Feb 27;130(8):2378-9. doi: 10.1021/ja076444d. Epub 2008 Feb 2.

Rhodium-catalyzed [(3+2)+2] carbocyclization of alkynylidenecyclopropanes with substituted allenes: stereoselective construction of tri- and tetrasubstituted exocyclic olefins.

Angew Chem Int Ed Engl. 2015 Apr 13;54(16):4768-72. doi: 10.1002/anie.201410857. Epub 2015 Feb 27.

Rhodium-catalyzed intramolecular [3+2+2] cycloadditions between alkylidenecyclopropanes, alkynes, and alkenes.

Chemistry. 2014 Aug 11;20(33):10255-9. doi: 10.1002/chem.201402473. Epub 2014 Jul 17.

引用本文的文献

Iron-Catalyzed Cycloisomerization and C-C Bond Activation to Access Non-canonical Tricyclic Cyclobutanes.

Angew Chem Int Ed Engl. 2022 Sep 19;61(38):e202205169. doi: 10.1002/anie.202205169. Epub 2022 Aug 8.

Transition metal catalyzed [6 + 2] cycloadditions.

RSC Adv. 2019 Aug 15;9(44):25554-25568. doi: 10.1039/c9ra02839k. eCollection 2019 Aug 13.

Intermolecular [5+2] Annulation between 1-Indanones and Internal Alkynes by Rhodium-Catalyzed C-C Activation.

Angew Chem Int Ed Engl. 2021 Sep 6;60(37):20476-20482. doi: 10.1002/anie.202106007. Epub 2021 Aug 3.

Transition Metal-Catalyzed Selective Carbon-Carbon Bond Cleavage of Vinylcyclopropanes in Cycloaddition Reactions.

Chem Rev. 2021 Jan 13;121(1):110-139. doi: 10.1021/acs.chemrev.0c00160. Epub 2020 Aug 5.

Enantioselective Rhodium-Catalyzed Cycloisomerization of 1,6-Allenynes to access 5/6-Fused Bicycle[4.3.0]nonadienes.

Nat Commun. 2019 Feb 27;10(1):949. doi: 10.1038/s41467-019-08900-z.

Ynol Ethers as Ketene Equivalents in Rhodium-Catalyzed Intermolecular [5 + 2] Cycloaddition Reactions.

Org Lett. 2017 Nov 3;19(21):5810-5813. doi: 10.1021/acs.orglett.7b02765.

Rhodium-Catalyzed Stereoselective Intramolecular [5 + 2] Cycloaddition of 3-Acyloxy 1,4-Enyne and Alkene.

Org Lett. 2015 Oct 16;17(20):5128-31. doi: 10.1021/acs.orglett.5b02665. Epub 2015 Oct 6.

J Am Chem Soc. 2014 Dec 10;136(49):17273-83. doi: 10.1021/ja5098308. Epub 2014 Nov 24.

3-Acyloxy-1,4-enyne: a New Five-carbon Synthon for Rhodium-Catalyzed (5+2) Cycloadditions.

Pure Appl Chem. 2014 Mar 1;86(3):409-417. doi: 10.1515/pac-2014-5042.

Transfer of chirality in the rhodium-catalyzed intramolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes (ACEs) and alkynes: synthesis of enantioenriched bicyclo[5.3.0]decatrienes.

Angew Chem Int Ed Engl. 2013 Dec 16;52(51):13601-5. doi: 10.1002/anie.201306919. Epub 2013 Oct 21.

Rhodium(I)-catalyzed intramolecular [5+2] cycloaddition reactions of alkynes and allenylcyclopropanes: construction of bicyclo[5.4.0]undecatrienes and bicyclo[5.5.0]dodecatrienes.

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Rhodium(I)-catalyzed intramolecular [5+2] cycloaddition reactions of alkynes and allenylcyclopropanes: construction of bicyclo[5.4.0]undecatrienes and bicyclo[5.5.0]dodecatrienes.

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