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Synthesis of Cyclic ?-Silylalkenyl Triflates via an Alkenyl Cation Intermediate.

ABSTRACT: Trimethylsilylalkyne derivatives are transformed into cyclic ?-silylalkenyl triflates through cationic cyclization and subsequent trapping of the alkenyl cation by a triflate anion. ?-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 ?-apopicropodophyllin.

SUBMITTER: Lee CJ

PROVIDER: S-EPMC6133754 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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Synthesis of Cyclic β-Silylalkenyl Triflates via an Alkenyl Cation Intermediate.

Lee Craig J CJ Swain Manisha M Kwon Ohyun O

Organic letters 20180817 17

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. ...[more]

PMID: 30118234

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