A palladium-catalyzed route to mono- and diprotected cis-2-cyclopentene-1,4-diols

✍ Scribed by Donald R. Deardorff; David C. Myles; Kurtis D. MacFerrin

• Publisher: Elsevier Science
• Year: 1985
• Tongue: French
• Weight: 215 KB
• Volume: 26
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)80901-1

✦ Synopsis

The n-allylpalladium complex arising from cyclopentadiene monoepoxide has been shown to react with carboxylic acids and derivatives both as a nucleophile and an electrophile. This reaction represents an attractive synthetic route to protected versions of cis-2-cyclopentene-1,4-diol.

We were intrigued by the synthetic potential inherent in zwitterions (2_) generated by the opening of vinyl epoxides (1> with palladium(O) catalysts (es 1).

Unlike other n-allylpalladium complexes, these dipolar intermediates harbor both a nucleophilic and an