The Direct and Enantioselective, One-Pot, Three-Component, Cross-Mannich Reaction of Aldehydes†
Yujiro Hayashi Prof. Dr.
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorWataru Tsuboi
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorItaru Ashimine
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorTatsuya Urushima
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorMitsuru Shoji Dr.
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorKen Sakai Prof. Dr.
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
Search for more papers by this authorYujiro Hayashi Prof. Dr.
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorWataru Tsuboi
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorItaru Ashimine
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorTatsuya Urushima
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorMitsuru Shoji Dr.
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, Fax: (+81) 3-5261-4631
Search for more papers by this authorKen Sakai Prof. Dr.
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
Search for more papers by this authorThis work was supported by a Grant-in-Aid for Scientific Research on Priority Areas (A; “Exploitation of Multi-Element Cyclic Molecules”) from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.
Graphical Abstract
Zweifach über Kreuz: Der Einsatz von Prolin als organischem Katalysator ermöglicht eine direkte gekreuzte Eintopf-Mannich-Reaktion zwischen zwei unterschiedlichen Aldehyden und 4-Methoxyanilin, die hochgradig syn-diastereo- und enantioselektiv abläuft.
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- 20Crystal data: C17H20ClNO2, monoclinic, space group P21, a=10.206(4), b=6.187(2), c=12.962(5) Å, β=97.838(6)°, V=810.8(5) Å3, Z=2, R1=0.1427, wR2=0.4094 (refined on F2 using SHELXL97). CCDC-212084 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or [email protected]).
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- 22HPLC conditions: Chiral AD-H column, iPrOH:hexane 1:30, 0.5 mL min−1, retention times: 74.6 min (minor) and 80.4 min (major).
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