4.8 Article

Synthesis of Functionalized Medium-Sized trans-Cycloalkenes by 4π Electrocyclic Ring Opening/Alkylation Sequence

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 34, Pages 11836-11840

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201906665

Keywords

cycloalkenes; electrocyclic reactions; medium-sized rings; planar chirality; synthetic methods

Funding

  1. Japan Agency for Medical Research and Development Funding Source: Medline
  2. Japan Society for the Promotion of Science [JP19H03350, JP 16H05073, JP17J10201] Funding Source: Medline
  3. Ministry of Education, Culture, Sports, Science and Technology [JP18H04406, JP16H01147] Funding Source: Medline
  4. Tokyo Kasei Chemical Promotion Foundation Funding Source: Medline

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Development of a novel synthetic method for medium-sized trans-cycloalkenes (TCAs) is described. Functionalized TCAs are readily prepared from simple cycloalkanones in a few steps, namely, enol silyl ether formation, [2+2] cycloaddition, and domino 4 pi electrocyclic ring opening/alkylation (conjugate addition). The first example of central-to-planar chirality transfer from enantiomerically enriched cyclobutenes to TCAs is also described.

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