通过远程立体控制实现1,3-和1,4-取代的环己基锌试剂与溴代炔烃之间的高度非对映选择性C(sp3)-C(sp)交叉偶联反应。 - Suppr

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Highly diastereoselective C(sp3)-C(sp) cross-coupling reactions between 1,3- and 1,4-substituted cyclohexylzinc reagents and bromoalkynes through remote stereocontrol.

作者信息

Thaler Tobias, Guo Li-Na, Mayer Peter, Knochel Paul

机构信息

Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, Haus F, 81377 München, Germany.

出版信息

Angew Chem Int Ed Engl. 2011 Feb 25;50(9):2174-7. doi: 10.1002/anie.201006879. Epub 2011 Feb 1.

DOI:10.1002/anie.201006879

PMID:21344579

Abstract

摘要

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Highly diastereoselective C(sp3)-C(sp) cross-coupling reactions between 1,3- and 1,4-substituted cyclohexylzinc reagents and bromoalkynes through remote stereocontrol.

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Highly diastereoselective C(sp3)-C(sp) cross-coupling reactions between 1,3- and 1,4-substituted cyclohexylzinc reagents and bromoalkynes through remote stereocontrol.

作者信息

Thaler Tobias, Guo Li-Na, Mayer Peter, Knochel Paul

机构信息

Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, Haus F, 81377 München, Germany.

出版信息

Angew Chem Int Ed Engl. 2011 Feb 25;50(9):2174-7. doi: 10.1002/anie.201006879. Epub 2011 Feb 1.

DOI:10.1002/anie.201006879

PMID:21344579

Abstract

摘要

相似文献

Highly diastereoselective C(sp3)-C(sp) cross-coupling reactions between 1,3- and 1,4-substituted cyclohexylzinc reagents and bromoalkynes through remote stereocontrol.

Angew Chem Int Ed Engl. 2011 Feb 25;50(9):2174-7. doi: 10.1002/anie.201006879. Epub 2011 Feb 1.

Palladium-catalyzed diastereoselective coupling of propargylic oxiranes with terminal alkynes.

Org Lett. 2007 Apr 26;9(9):1643-6. doi: 10.1021/ol070224n. Epub 2007 Mar 28.

Enantioselective nickel-catalyzed cross-coupling reactions of trialkynylindium reagents with racemic secondary benzyl bromides.

Chemistry. 2008;14(2):741-6. doi: 10.1002/chem.200701035.

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Angew Chem Int Ed Engl. 2007;46(6):834-71. doi: 10.1002/anie.200602761.

Fused ring construction around pyrrole, indole, and related compounds via palladium-catalyzed oxidative coupling with alkynes.

J Org Chem. 2009 Oct 2;74(19):7481-8. doi: 10.1021/jo9016698.

Synthesis of highly substituted 1,3-butadienes by palladium-catalyzed arylation of internal alkynes.

Angew Chem Int Ed Engl. 2004 Sep 27;43(38):5063-5. doi: 10.1002/anie.200460409.

Synthesis of indenes by the palladium-catalyzed carboannulation of internal alkynes.

Org Lett. 2005 Oct 27;7(22):4963-6. doi: 10.1021/ol051907a.

Cationic palladium(II)-catalyzed highly enantioselective [3+2] annulation of 2-acylarylboronic acids with substituted alkynes.

Org Lett. 2007 Nov 22;9(24):5131-3. doi: 10.1021/ol702503e. Epub 2007 Nov 2.

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Org Lett. 2010 Jul 2;12(13):3006-9. doi: 10.1021/ol101012n.

Palladium-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with arylboronic acids.

Chem Commun (Camb). 2010 Jul 14;46(26):4779-81. doi: 10.1039/c0cc00403k. Epub 2010 May 20.

引用本文的文献

Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis.

Chem Rev. 2024 Dec 11;124(23):13397-13569. doi: 10.1021/acs.chemrev.4c00524. Epub 2024 Nov 26.

Cobalt-catalyzed conformationally restricted alkylarylation enables divergent access to Csp-rich N-heterocycles.

Chem Sci. 2024 Sep 3;15(39):16250-8. doi: 10.1039/d4sc04056b.

Cobalt-Catalyzed Cross-Coupling of Functionalized Alkylzinc Reagents with (Hetero)Aryl Halides.

Angew Chem Int Ed Engl. 2020 Mar 27;59(14):5546-5550. doi: 10.1002/anie.201914490. Epub 2020 Feb 18.

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Angew Chem Int Ed Engl. 2017 Sep 18;56(39):11901-11905. doi: 10.1002/anie.201706781. Epub 2017 Aug 17.

Coupling of α,α-difluoro-substituted organozinc reagents with 1-bromoalkynes.

Beilstein J Org Chem. 2015 Nov 10;11:2145-9. doi: 10.3762/bjoc.11.231. eCollection 2015.

Copper-catalyzed oxidative homo- and cross-coupling of Grignard reagents using diaziridinone.

Org Lett. 2014 Dec 5;16(23):6144-7. doi: 10.1021/ol5030103. Epub 2014 Nov 24.

The Use of Tertiary Alkylmagnesium Nucleophiles in Ni-Catalyzed Cross-Coupling Reactions.

Synlett. 2012 May 14;23(8):1103-1107. doi: 10.1055/s-0031-1290765.