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Enantioselective Synthesis of Complementary Double-Helical Molecules that Catalyze Asymmetric Reactions

Authors

  • Takashi Hasegawa,

    1. Yashima Super-structured Helix Project, Exploratory Research for Advanced Technology (ERATO), Japan Science and Technology Agency (JST), 101 Creation Core Nagoya, 2266-22 Anagahora, Shimoshidami, Moriyama-ku, Nagoya 463-0003, Japan, Fax: (+81) 52-739-2084
    2. Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan, Fax: (+81) 52-789-3185
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  • Yoshio Furusho Dr.,

    1. Yashima Super-structured Helix Project, Exploratory Research for Advanced Technology (ERATO), Japan Science and Technology Agency (JST), 101 Creation Core Nagoya, 2266-22 Anagahora, Shimoshidami, Moriyama-ku, Nagoya 463-0003, Japan, Fax: (+81) 52-739-2084
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  • Hiroshi Katagiri Dr.,

    1. Yashima Super-structured Helix Project, Exploratory Research for Advanced Technology (ERATO), Japan Science and Technology Agency (JST), 101 Creation Core Nagoya, 2266-22 Anagahora, Shimoshidami, Moriyama-ku, Nagoya 463-0003, Japan, Fax: (+81) 52-739-2084
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  • Eiji Yashima Prof.

    1. Yashima Super-structured Helix Project, Exploratory Research for Advanced Technology (ERATO), Japan Science and Technology Agency (JST), 101 Creation Core Nagoya, 2266-22 Anagahora, Shimoshidami, Moriyama-ku, Nagoya 463-0003, Japan, Fax: (+81) 52-739-2084
    2. Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan, Fax: (+81) 52-789-3185
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  • We thank Bruker AXS K.K. for providing generous access to the Bruker Smart Apex II CCD-based X-ray diffractometer. We also acknowledge Dr. Hiroshi Ito (JST) for his help with the X-ray single-crystal analysis.

Abstract

original image

Two twisted: Optically active double helices were synthesized through a twist-sense bias induced by a chiral phosphine ligand on one of the complementary metallostrands followed by a ligand-exchange reaction with an achiral bidentate ligand, which replaces the chiral ligand, to bridge the two strands. Furthermore, the double helices can efficiently catalyze asymmetric cyclopropanation.

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