PRINTER FRIENDLY THESIS ABSTRACTS

Last name:
Title of Thesis or Name of the Project:

Database ID: 840

Name: Schreiber, Jürg
Title of Thesis or Name of the Project: Preparation of Vinyl Triflates from Vinyl TBDMS Ethers
Thesis Abstract: The conversion of silyl enol ethers into the corresponding enol triflates was developed. A systematic investigation of different reaction conditions with respect to improve the yield for this conversion provided the following result: treatment of the silyl enol ether with CsF and PhNTf2 in DME at room temperature in a sealed tube is the method of choice for this transformation. The process is quite general. This new transformation enabled an exceedingly short (four steps) and effective total synthesis of (+)-α-onocerin starting with a chiral epoxy ketone (Yuan Mi). In a key step of the total synthesis a bis-enol silane was converted into the corresponding bis-enol triflate in good yield (72%).