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Diastereo- and Atroposelective Synthesis of Bridged Biaryls Bearing an Eight-Membered Lactone through an Organocatalytic Cascade.

08:00 EDT 11th October 2019 | BioPortfolio

Summary of "Diastereo- and Atroposelective Synthesis of Bridged Biaryls Bearing an Eight-Membered Lactone through an Organocatalytic Cascade."

We present herein an unprecedented stereoselective synthesis of bridged biaryls with defined axial and central chirality from readily available starting materials. This NHC-catalyzed method proceeds through propargylic substitution of azolium enolates followed by two-directional cyclization as supported by DFT calculation. A range of benzofuran/indole-derived bridged biaryls bearing an eight-membered lactone are accessed with uniformly high stereoselectivity (>98:2 dr, mostly >98% ee).

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