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A Borate Propeller Compound as Chiral Catalyst for an Asymmetrically Induced Diels‐Alder Reaction

1990; Wiley; Volume: 29; Issue: 5 Linguagem: Inglês

10.1002/anie.199005451

1521-3773

Dieter Kaufmann, Roland Boese,

Axial and Atropisomeric Chirality Synthesis

Angewandte Chemie International Edition in EnglishVolume 29, Issue 5 p. 545-546 Communication A Borate Propeller Compound as Chiral Catalyst for an Asymmetrically Induced Diels-Alder Reaction Priv.-Doz. Dr. Dieter Kaufmann, Corresponding Author Priv.-Doz. Dr. Dieter Kaufmann Bayer AG, Zentraie Forschung und Entwicklung D-5090 Leverkusen (FRG)Bayer AG, Zentraie Forschung und Entwicklung D-5090 Leverkusen (FRG)Search for more papers by this authorDr. Roland Boese, Dr. Roland Boese Institut für Anorganische Chemie der Universität-Gesamthochschule Essen, Universitätsstrasse 3–5, D-4300 Essen 1 (FRG)Search for more papers by this author Priv.-Doz. Dr. Dieter Kaufmann, Corresponding Author Priv.-Doz. Dr. Dieter Kaufmann Bayer AG, Zentraie Forschung und Entwicklung D-5090 Leverkusen (FRG)Bayer AG, Zentraie Forschung und Entwicklung D-5090 Leverkusen (FRG)Search for more papers by this authorDr. Roland Boese, Dr. Roland Boese Institut für Anorganische Chemie der Universität-Gesamthochschule Essen, Universitätsstrasse 3–5, D-4300 Essen 1 (FRG)Search for more papers by this author First published: May 1990 https://doi.org/10.1002/anie.199005451Citations: 97AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Three binaphthyl groups as "blades" have been joined together to give the propeller compound 1. The synthesis of this compound proved surprisingly easy via reaction of a borane with optically active 1,1′-bi-2-naphthol. Compound 1 is more than just "a cute molecule"; it also catalyzes a highly exo and enantioselective Diels–Alder reaction of cyclopentadiene with methacrolein. References 1 K. Krohn, Nachr. Chem. Tech. Lab. 35 (1987) 836. 2 G. Bir, D. Kaufmann, Tetrahedron Lett. 28 (1987) 777. 3 U.-M. Gross, M. Bartels, D. Kaufmann, J. Organomet. Chem. 344 (1988) 277. 4 F. Toda, K. Tanaka, L. Nassimbeni, M. Niven, Chem. Lett. 1988, 1371. 5 H. C. Brown, N. Ravindran, Inorg. Chem. 16 (1977) 2938. 6 T. R. Kelly, A. Whiting, N. S. Chandrakumar, J. Am. Chem. Soc. 108 (1986) 3510. 7 X-ray structure analysis of 5 at room temperature, crystal growth at 0°C from pentane/dichloromethane (2/1); the unit cell contained one molecule of dichloromethane: P1. a = 9.3537(10), b = 14.4558(13), c = 19.1677(19) Å, α = 111.931(7). β = 91.371(8). γ = 100.487(8)°, V = 2352.2(4) Å3, Z = 2. ϱcalc, = 1.335 gcm−3; Mokα radiation (graphite monochromator). scan range 3° ≤ 2Θ ≤ 50°; total number of reflections: 8272, observed reflections: 5749 (Fo ≥ 4σ(F)), R = 0.0526, Rw = 0.0612, Nicolet-R3m/V four-circle X-ray diffractometer, data calculated with SHELXTL-PLUS on a MicroVAX II.—Further details of the crystal structure investigation are available on request from the Fachinformationsezentrum Karlsruhe, Gsellschaft für wissenschaftlich-technische. Information mbH, D−7514 Eggenstein-Leopoldshafen 2(FRG) on quoting the depository number CDS−320095, the names of the authors, and the journal citation. 8 K. Furuta, S. Shimizu, Y. Miwa, H. Yamamoto, J. Org. Chem. 54 (1989) 9 Y. Kobuke, T. Fueno, J. Furukawa, J. Am. Chem. Soc. 92 (1970) 6548. 10 Aldrich Chemical Company, Inc. Citing Literature Volume29, Issue5May 1990Pages 545-546 ReferencesRelatedInformation