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16 results on '"Tripoteau, Fabien"'

4. [3]-1-Azadendralenes as Versatile Building Blocks for the Stereoselective Synthesis of Polysubstituted Hexahydroquinazolin-2-ones and Hexahydrobenzothiazine-2-­imines

Author

Kobayashi, Satoru, Kudo, Kenji, Ito, Ai, Honjo, Takuya, Yata, Masahiro, Otani, Takashi, Kutsumura, Noriki, Saito, Takao, Berrée, Fabienne, Romain, Elise, Tripoteau, Fabien, Carboni, Bertrand, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institut Parisien de Chimie Moléculaire (IPCM), and Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Synthetic methods, Molecular diversity, Nitrogen heterocycles, [CHIM]Chemical Sciences, Cycloaddition
Abstract

International audience; A diene-transmissive hetero-Diels–Alder reaction of cross-conjugated 1-azatrienes (3-1-azadendralenes) is described for the synthesis of hexahydroquinazolin-2-ones and hexahydrobenzothiazine-2-imines derivatives. [4+2] Cycloaddition reactions with tosyl isocyanate or aryl isothiocyanates gave mono-cycloadducts with high chemo- and regioselectivities. The second Diels–Alder reaction with representative dienophiles, tetracyanoethylene, N-phenylmaleimide, and methyl vinyl ketone, stereoselectively produced ring-fused nitrogen heterocycles. Skeletal diversity can be accessed by combining the three reaction partners – primary amine, tosyl isocyanate, and cross-conjugated 1-oxatriene – in a different sequential order

Published
2015

15. Bleaching Earths as Powerful Additives for Ru-Catalyzed Self-Metathesis of Non-Refined Methyl Oleate at Pilot Scale.

Author

Allard J, Curbet I, Chollet G, Tripoteau F, Sambou S, Caijo F, Raoul Y, Crévisy C, Baslé O, and Mauduit M

Subjects
Catalysis, Stearic Acids chemistry, Stereoisomerism, Oleic Acids chemistry, Ruthenium chemistry
Abstract

A practical and cost-effective ruthenium-catalyzed self-metathesis of non-refined methyl oleate (85 %) derived from very high oleic sunflower oils was demonstrated at pilot scale using a robust and kg-scale commercially available SIPr-M71 pre-catalyst. The simple addition of 1 wt % bleaching earths (Tonsil 110FF) to a thermally pretreated oil could efficiently prevent catalyst deactivation. Remarkably, without the need for filtration, the catalytic system was able to achieve a turnover number (TON) of more than 744 000 at a catalyst loading of only 1 ppm. At large scale (up to 200 kg), the equilibrium of the self-metathesis reaction was reached within 1 hour at 50 °C under neat conditions at a very low 5 ppm catalyst loading to produce the expected primary metathesis products (PMP), that is, 9-octadecene and dimethyl-9-octadecenoate, with a productive TON of 94900., (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2017
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