Allylic sulfones in solid-phase synthesis: Preparation of cyclobutylidenes

Wei Chieh Cheng, Chris Halm, Jerry B. Evarts, Marilyn M. Olmstead, Mark J. Kurth

Research output: Contribution to journalArticle

49 Scopus citations

Abstract

Polymer-bound allyl sulfones (cf. 9) were utilized in geminal cycloalkylations with epichlorohydrin to generate a cis- phenylsulfonylcyclobutanol derivative (cf. 11) in one step. In the final step of this solid-phase synthetic sequence, cuprate, organomolybdenum, and organopalladium reagents were screened to obtain an optimal protocol for 'traceless' cleavage of cyclobutylidene products from the resin. Among these, palladium-catalyzed allylic alkylation was the most efficient. In addition, highly regioselective nucleophilic attack at the less hindered terminus of the allyl fragment (i.e., overall S(N)2' sulfinate displacement) was observed. Cyclobutylidene diversification was demonstrated by incorporating different allylic substituents, O-functionalizations, and C-nucleophiles to prepare a demonstration library of eight cyclobutylidene derivatives (i.e., derivatives of 4) in four steps and 30-38% overall yield from lithium polystyrene/divinylbenzene sulfinate.

Original languageEnglish (US)
Pages (from-to)8557-8562
Number of pages6
JournalJournal of Organic Chemistry
Volume64
Issue number23
DOIs
StatePublished - Nov 12 1999

ASJC Scopus subject areas

  • Organic Chemistry

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    Cheng, W. C., Halm, C., Evarts, J. B., Olmstead, M. M., & Kurth, M. J. (1999). Allylic sulfones in solid-phase synthesis: Preparation of cyclobutylidenes. Journal of Organic Chemistry, 64(23), 8557-8562. https://doi.org/10.1021/jo990954b