The molecular structures of (+)-6-benzylsparteine, (ethyl)(bromo)((+)-6-benzylsparteine)magnesium(II), and dibromo((+)-6-benzylsparteine)magnesium(II). Structure and reactivity of the Grignard reagent-(-)-sparteine derivative complexes for asymmetric sele

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• (+)-6-Benzylsparteine (<B>a</B>) crystallizes in orthorhombic systems; <I>P</I>2<SUB>1</SUB>2<SUB>1</SUB>2<SUB>1</SUB>, <I>a</I>=10.711(1), <I>b</I>=25.868(4), <I>c</I><SUB>=</SUB>6.804(1) Å, and <I>Z</I>=4;EtMgBr-(+)-6-benzylsparteine (<B>b</B>) also belongs to orthorhombic system; <I>P</I>2<SUB>1</SUB>2<SUB>1</SUB>2<SUB>1</SUB>, <I>a</I>=11.020(4), <I>b</I>=23.660(10), <I>c</I>=8.666(6) Å and <I>Z</I>=4; and MgBr<SUB>2</SUB>−(+)-6-benzylsparteine toluene solvate (<B>c</B>), orthorhombic system; <I>P</I>2<SUB>1</SUB>2<SUB>1</SUB>2<SUB>1</SUB>, <I>a</I>=16.654(3), <I>b</I>=19.723(4), <I>c</I>=8.637(2) Å and <I>Z</I>=4. The structure of <B>a</B> was solved by the direct method and those of <B>b</B> and <B>c</B> by the heavy atom method. Refinements were carried out by the block-diagonal least-squares procedure; <I>R</I> values are: (<B>a</B>) 0.055. (<B>b</B>) 0.169, and (<B>c</B>) 0.118, respectively for 1342, 1445, and 1501 reflections. The <B>a</B> molecule takes a one-boat form, whereas by, coordination to the Mg atom it changes into all-chair form in <B>b</B> and <B>c</B> molecules. The Mg atom has a distorted tetrahedral geometry; <B>b</B>, Mg–N=2.13(4) and 2.19(4), Mg–C 2.34(5) and Mg–Be=2.506(16) Å and N–Ng–N=83.1(14)°; <B>c</B>, Mg–N=2.08(3) and 2.17(3), Mg–Br=2.454(12) and 2.473(12) Å and N–Mg–N=85.8(10)°. The structures of these molecules are compared with those of (−)-sparteine complexes with EtMgBr, <I>t</I>-BuMgCl, and MgCl<SUB>2</SUB>. On the basis of the molecular structures determined the activity of these Grignard reagent–(−)-sparteine derivatives for the enantiomer-selective polymerization of MBMA is discussed.

• 公益社団法人 日本化学会の論文

著者

• Miki Kunio

  Department Of Chemistry Graduate School Of Science Kyoto University

• Kai Yasushi

  Department Of Applied Chemistry Faculty Of Engineering Osaka University

• Kageyama Hiroyuki

  Department For Energy Conversion Osaka National Research Institute

• Kasai Nobutami

  Department Of Applied Biological Science Tokyo University Of Science

• Okamoto Yoshio

  Department Of Applied Chemistry Faculty Of Engineering Nagoya University

• Yuki Heimei

  Department of Polymer Science Faculty of Science Osaka University

• Miki Kunio

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

• Yuki Heimei

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

• Kageyama Hiroyuki

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

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