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Axially Chiral Binaphthyl Surrogates with an Inner N−H−N Hydrogen Bond

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Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
[email protected]
Cite this: J. Am. Chem. Soc. 2009, 131, 1, 54–55
Publication Date (Web):December 18, 2008
https://doi.org/10.1021/ja808213r
Copyright © 2008 American Chemical Society
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Abstract

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Novel chiral binaphtyl surrogates with an inner hydrogen bond have been created. The N—H appears at 13.0−13.3 ppm in thier 1H NMR spectrum, indicating extremely strong hydrogen bonding. Enantiomers of these compounds were stable at ambient temperature and separable by HPLC with a chiral stationary phase. The half-lives of racemization of the enantiomer are in the range 3 months to 2 years at 20 °C, and the barriers for racemization are in the range 27.0 to 28.2 kcal/mol. An X-ray crystal analysis of the compound (R = CHPh2) shows that the pseudonaphthyl skeleton including C═N···H—N is almost completely planar and the dihedral angle between the pseudonaphthalene and naphthalene rings is 128°.

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  14. Yudai Morimoto, Satoshi Shimizu, Ayano Mokuya, Nobutaka Ototake, Akio Saito, Osamu Kitagawa. Enantioselective synthesis of N–C axially chiral indoles through chiral palladium-catalyzed 5-endo-hydroaminocyclization. Tetrahedron 2016, 72 (34) , 5221-5229. https://doi.org/10.1016/j.tet.2015.05.001
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  19. Isao Takahashi, Yuya Suzuki, Osamu Kitagawa. Asymmetric Synthesis of Atropisomeric Compounds with an N‒C Chiral Axis. Organic Preparations and Procedures International 2014, 46 (1) , 1-23. https://doi.org/10.1080/00304948.2014.866467
  20. Isao Takahashi, Fumika Morita, Shunsuke Kusagaya, Haruhiko Fukaya, Osamu Kitagawa. Catalytic enantioselective synthesis of atropisomeric 2-aryl-4-quinolinone derivatives with an N–C chiral axis. Tetrahedron: Asymmetry 2012, 23 (24) , 1657-1662. https://doi.org/10.1016/j.tetasy.2012.11.004
  21. Tomoyuki Yoshimura. Asymmetric Synthesis of Multi-substituted β-Lactams via C-N Axially Chiral Enolates in Intramolecular Conjugate Addition. YAKUGAKU ZASSHI 2012, 132 (11) , 1287-1295. https://doi.org/10.1248/yakushi.12-00217
  22. T. Furuta, T. Kawabata. 6.17 C–O Bond Formation: Acylation of meso Diols. 2012,,, 434-451. https://doi.org/10.1016/B978-0-08-095167-6.00619-4
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  25. Takashi Mino, Haruka Yamada, Shingo Komatsu, Mizuki Kasai, Masami Sakamoto, Tsutomu Fujita. Atropisomerism at C-N Bonds of Acyclic Amines: Synthesis and Application to Palladium-Catalyzed Asymmetric Allylic Alkylations. European Journal of Organic Chemistry 2011, 2011 (24) , 4540-4542. https://doi.org/10.1002/ejoc.201100769
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  29. Kazuhiro Hayashi, Yumiko Nakajima, Fumiyuki Ozawa, Takeo Kawabata. Axially Chiral Anilido–Aldimine Aluminum Complexes with a Pseudobinaphthyl Skeleton. Chemistry Letters 2010, 39 (6) , 643-645. https://doi.org/10.1246/cl.2010.643
  30. Masashi Takahashi, Hajime Tanabe, Tsuyoshi Nakamura, Daisuke Kuribara, Toshiyuki Yamazaki, Osamu Kitagawa. Atropisomeric lactam chemistry: catalytic enantioselective synthesis, application to asymmetric enolate chemistry and synthesis of key intermediates for NET inhibitors. Tetrahedron 2010, 66 (1) , 288-296. https://doi.org/10.1016/j.tet.2009.10.095
  31. Naoya Shindoh, Yoshiji Takemoto, Kiyosei Takasu. Atropisomerism of α,β-Unsaturated Amidines: Stereoselective Synthesis by Catalytic Cascade Reaction and Optical Resolution. Chemistry - A European Journal 2009, 15 (29) , 7026-7030. https://doi.org/10.1002/chem.200901103

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