Absolute structure determination of compounds with axial and planar chirality using the crystalline sponge method.

نویسندگان

  • Shota Yoshioka
  • Yasuhide Inokuma
  • Manabu Hoshino
  • Takashi Sato
  • Makoto Fujita
چکیده

The absolute stereochemistry of compounds with axial and planar chirality is successfully determined by the crystalline sponge method without crystallization or derivatization of the compounds. This method is applied to absolute structure determination in the asymmetric synthesis of unique compounds with axial and planar chirality.

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منابع مشابه

Absolute structure determination of compounds with axial and planar chirality using the crystalline sponge method† †Electronic supplementary information (ESI) available: Details of sample preparation and crystallographic analysis. CCDC 1051799, 1051800, 1051618, 1051619, 1043948 and 1043949. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc01681a Click here for additional data file. Click here for additional data file.

Chiral molecules with axial or planar chirality are of special interest to synthetic chemists because of both their unique chirality without stereogenic centers and their practical use as chiral auxiliaries or chiral ligands for catalytic asymmetric syntheses. There are therefore a number of reports on the asymmetric synthesis of these chiral molecules. Unlike common chiral molecules with stere...

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Determination of the absolute configuration of compounds bearing chiral quaternary carbon centers using the crystalline sponge method.

Determination of the absolute configuration of chiral tetra-substituted carbon centers is one of the most taxing steps in the enantioselective construction of this structural motif in asymmetric synthesis. Here, we demonstrate that the crystalline sponge method provides an effective way to crystallographically determine the absolute configuration of organic compounds bearing chiral quaternary c...

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Cycloelatanene A and B: absolute configuration determination and structural revision by the crystalline sponge method.

Cycloelatanene A and B are marine natural products first reported a few years ago. Their relative structures had been elucidated by an extensive NMR study and found to be epimers. However, their absolute configurations had not been established because they were isolated in only minute quantities as oily compounds. In this study, the complete structures of cycloelatanene A and B, including absol...

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Cycloelatanene A and B: absolute configuration determination and structural revision by the crystalline sponge method† †Electronic supplementary information (ESI) available. CCDC 1487142 and 1487143. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc04288k Click here for additional data file. Click here for additional data file.

Cycloelatanene A and B are marine natural products first reported a few years ago. Their relative structures had been elucidated by an extensive NMR study and found to be epimers. However, their absolute configurations had not been established because they were isolated in only minute quantities as oily compounds. In this study, the complete structures of cycloelatanene A and B, including absol...

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Determination of the absolute configuration of compounds bearing chiral quaternary carbon centers using the crystalline sponge method† †Electronic supplementary information (ESI) available: Details of sample preparation and crystallographic analysis. CCDC 1492160–1492163 and 1537112. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc01524k Click here for additional data file. Click here for additional data file.

Department of Applied Chemistry, School 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-865 u-tokyo.ac.jp JST ACCEL, 4-1-8 Honcho, Kawaguchi, Sait The Institute of Scientic and Industri Mihogaoka, Ibaraki-shi, Osaka 567-0047, Ja Institute of Transformative Bio-Molecules 464-8602, Japan † Electronic supplementary information preparation and crystallographic ana 1537112. For ESI and crystallographic dat DOI: ...

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عنوان ژورنال:
  • Chemical science

دوره 6 7  شماره 

صفحات  -

تاریخ انتشار 2015