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Synlett 1998; 1998(8): 915-917
DOI: 10.1055/s-1998-1810
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A Facile Oxidation/Deprotection of Electron Rich Silyl Ethers Using DDQ

Ian Paterson* , Cameron J. Cowden, Volker S. Rahn, Michael D. Woodrow
  • *University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK; Fax + 44 1223 33 63 62; E-mail: ip100@cus.cam.ac.uk; Website: http://www-paterson.ch.cam.ac.uk
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Publication History

Publication Date:
31 December 2000 (online)

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The selective oxidation/deprotection of allylic and benzylic silyl ethers to give aldehydes can be achieved by hydride abstraction with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under neutral conditions. This reaction is possible in the presence of a variety of silyl protecting groups, as in 2 → 3, and even PMB ethers and PMP acetals, as in 14 → 15, which are normally labile under DDQ oxidation conditions.

DDQ - oxidation - deprotection - silyl ether - aldehyde