4.3 Article

Stereoselective Synthesis of Allylsilanes Bearing Tetrasubstituted Olefin via 2,2-Diborylethylsilane

Journal

CHEMISTRY LETTERS
Volume 40, Issue 12, Pages 1440-1442

Publisher

CHEMICAL SOC JAPAN
DOI: 10.1246/cl.2011.1440

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Funding

  1. JST PRESTO
  2. Japan Society for the Promotion of Science
  3. Grants-in-Aid for Scientific Research [23750049] Funding Source: KAKEN

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The regio- and stereoselective synthesis of allylsilane derivatives bearing a tetrasubstituted olefin was achieved using 2,2-diborylethylsilane as a key intermediate. The regioselective deprotonation of a 2,2-diborylethylsilane with LTMP and the subsequent nucleophilic addition to ketones gave corresponding allylsilanes in good to excellent yield with excellent stereoselectivity.

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