4.8 Article

Enantioselective Synthesis of [9]- and [11]Helicene-like Molecules: Double Intramolecular [2+2+2] Cycloaddition

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 32, Pages 8480-8483

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201404810

Keywords

alkynes; cycloaddition; enantioselectivity; helical structures; rhodium

Funding

  1. ACT-C from Japan Science and Technology Agency (Japan)
  2. Ministry of Education, Culture, Sports, Science and Technology (Japan) [20675002]
  3. Grants-in-Aid for Scientific Research [25105714, 13J08112, 26102004] Funding Source: KAKEN

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The enantioselective synthesis of completely ortho-fused [9]- and [11] helicene-like molecules has been achieved through a rhodium-mediated, intramolecular, double [2+2+2] cycloaddition of phenol-or 2-naphthol-linked hexaynes. Crystal structures and photophysical properties of these [9]- and [11] helicene-like molecules have also been disclosed.

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