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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Synthesis of Cyclic β-Silylalkenyl Triflates via an Alkenyl Cation Intermediate
Craig J Lee1, Manisha Swain1, Ohyun Kwon1
1Department of Chemistry and Biochemistry , University of California, Los Angeles , 607 Charles E. Young Drive East , Los Angeles , California 90095-1569 , United States.
Abstract:
Trimethylsilylalkyne derivatives are transformed into cyclic β-silylalkenyl triflates through cationic cyclization and subsequent trapping of the alkenyl cation by a triflate anion. β-Silylcyclohexenyl triflates and 3-trimethylsilyl-1,4-dihydronaphth-2-yl triflates are generated efficiently using this methodology. These products provide ready access to substituted cyclohexynes, exemplified by a concise total synthesis of β-apopicropodophyllin.
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