Literature DB >> 12240403

Catalytic asymmetric synthesis of 1,1'-spirobi[indan-3,3'-dione] via a double intramolecular C-H insertion process.

T Takahashi1, H Tsutsui, M Tamura, S Kitagaki, M Nakajima, S Hashimoto.   

Abstract

A highly efficient one-pot construction of optically active 1,1'-spirobi[indan-3,3'-dione] derivative (up to 80% ee) has been achieved by exploiting the double intramolecular C-H insertion reaction of dimethyl 2,2'-methylenebis(alpha-diazo-beta-oxobenzenepropanoate) under the influence of dirhodium(II) tetrakis[N-phthaloyl-(R or S)-tert-leucinate] as a catalyst.

Entities:  

Year:  2001        PMID： 12240403     DOI： 10.1039/b103747c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  6 in total

1.  Rhodium-catalyzed enantioselective vinylogous addition of enol ethers to vinyldiazoacetates.

Authors:  Austin G Smith; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2012-10-29       Impact factor: 15.419

2.  Asymmetric [4 + 3] cycloadditions between vinylcarbenoids and dienes: application to the total synthesis of the natural product (-)-5-epi-vibsanin E.

Authors:  Brett D Schwartz; Justin R Denton; Yajing Lian; Huw M L Davies; Craig M Williams
Journal:  J Am Chem Soc       Date:  2009-06-17       Impact factor: 15.419

Review 3.  Synthesis of 1-indanones with a broad range of biological activity.

Authors:  Marika Turek; Dorota Szczęsna; Marek Koprowski; Piotr Bałczewski
Journal:  Beilstein J Org Chem       Date:  2017-03-09       Impact factor: 2.883

4.  Stereoselective Radical C-H Alkylation with Acceptor/Acceptor-Substituted Diazo Reagents via Co(II)-Based Metalloradical Catalysis.

Authors:  Xin Cui; Xue Xu; Li-Mei Jin; Lukasz Wojtas; X Peter Zhang
Journal:  Chem Sci       Date:  2015-02       Impact factor: 9.825

5.  Catalytic Enantioselective Synthesis of C1 - and C2 -Symmetric Spirobiindanones through Counterion-Directed Enolate C-Acylation.

Authors:  Benjamin F Rahemtulla; Hugh F Clark; Martin D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

6.  Synthesis of amino acids and peptides with bulky side chains via ligand-enabled carboxylate-directed γ-C(sp3)-H arylation.

Authors:  Lei Liu; Yan-Hua Liu; Bing-Feng Shi
Journal:  Chem Sci       Date:  2019-11-11       Impact factor: 9.825
  6 in total

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