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1. Asymmetric synthesis of chiral trifluoromethylated heliotridane viahighly catalytic asymmetric Friedel–Crafts alkylation with β-trifluoromethylated acrylates and pyrrolesWe briefly communicated this work in 2010.23In the present paper, we describe in full the results of our highly catalytic asymmetric Friedel–Crafts alkylation.Electronic supplementary information (ESI) available: General experimental procedures, 1H, 13C and 19F NMR spectra for all crossed products, characterisation data for all new products. CCDC 758056. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c1nj20550a

Author

Huang, Yiyong, Suzuki, Satoru, Liu, Guokai, Tokunaga, Etsuko, Shiro, Motoo, and Shibata, Norio

Subjects
*ASYMMETRY (Chemistry), *CHIRALITY, *PYRROLIZIDINES, *ORGANIC synthesis, *CATALYSTS, *ACRYLATES, *PYRROLES, *CHEMICAL reactions
Abstract

Chiral Ph-dbfox (Ph-dbfox = (R,R)-4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline))/Zn(NTf2)2catalyzed enantioselective Friedel–Crafts reactions of β-CF3acrylates with pyrroles and indoles have been investigated, which afforded the corresponding chiral trifluoromethyl pyrrole and indole derivatives in high yields (90–99%) with a range of 66–99% ee values. With the aid of the chiral adduct of the asymmetric Friedel–Crafts reaction, the chiral trifluoromethylated heliotridane has been successfully constructed in good total yield. [ABSTRACT FROM AUTHOR]

Published
2011
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2. Cross-metathesis transformations of terpenoids in dialkyl carbonate solventsThis paper was published as part of the themed issue of contributions from the Green Solvents – Alternative Fluids in Science and Application conference held in Berchtesgaden, October 2010.Electronic supplementary information (ESI) available: Experimental procedures and products characterisations. See DOI: 10.1039/c1gc15024c

Author

Bilel, Hallouma, Hamdi, Naceur, Zagrouba, Fethy, Fischmeister, Cédric, and Bruneau, Christian

Subjects
*METATHESIS reactions, *TERPENES, *CARBONATES, *SOLVENTS, *RUTHENIUM compounds, *METHYL acrylate, *ORGANIC synthesis, *CHEMICAL reactions, *CATALYSTS
Abstract

The ruthenium catalysed cross-metathesis of terpenoids with methyl acrylate and methyl methacrylate was used to prepare new terpenoids and to improve, to a large extent, the synthesis of known terpenoids. In particular, the cross-metathesis of mono-unsaturated terpenoids was very efficient whereas the transformation of terpenoids incorporating two double bonds was more difficult due to side reactions. The cross-metathesis reactions were carried out under environmentally friendly conditions either in dimethyl carbonate or under solvent-free conditions. [ABSTRACT FROM AUTHOR]

Published
2011
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3. Direct catalytic asymmetric aldol reaction of β-keto esters with formaldehyde promoted by a dinuclear Ni2-Schiff base complexThis article is part of a ChemComm ‘Catalysis in Organic Synthesis’ web-theme issue showcasing high quality research in organic chemistry. Please see our website (http://www.rsc.org/chemcomm/organicwebtheme2009) to access the other papers in this issue.Electronic supplementary information (ESI) available: General experimental information, spectral data of new compounds, and copies of NMR spectral data. See DOI: 10.1039/b912380f

Author

Shinsuke Mouri, Zhihua Chen, Shigeki Matsunaga, and Masakatsu Shibasaki

Subjects
*CATALYSTS, *ASYMMETRY (Chemistry), *CHEMICAL reactions, *ESTERS, *FORMALDEHYDE, *COMPLEX compounds, *ORGANIC synthesis, *METHYLATION
Abstract

A homodinuclear Ni2-Schiff base 1complex (0.1–1 mol%) promoted the direct catalytic asymmetric aldol reaction of β-keto esters with formaldehyde, giving hydroxymethylated adducts in 94–66% ee. [ABSTRACT FROM AUTHOR]

Published
2009
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