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Catalytic and Asymmetric Process via P/P=O Redox Cycling: Access to (Trifluoromethyl)cyclobutenes via a Michael Addition/Wittig Olefination Reaction.

08:00 EDT 13th June 2019 | BioPortfolio

Summary of "Catalytic and Asymmetric Process via P/P=O Redox Cycling: Access to (Trifluoromethyl)cyclobutenes via a Michael Addition/Wittig Olefination Reaction."

In the present study, we report the first enantioselective and highly efficient phosphine-catalyzed process via a chemoselective in situ phosphine oxide reduction. Starting with 4,4,4-trifluorobutane-1,3-dione and dialkyl acetylenedicarboxylate substrates, highly functionalized fluorinated cyclobutenes were obtained in excellent yields and enantioselectivities. Using the same methodology, CF-spirocyclobutene derivatives were also synthesized (34 examples, up to 95% ee).

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Name: Journal of the American Chemical Society
ISSN: 1520-5126
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