American Chemical Society
ol9b00691_si_001.pdf (11.75 MB)

Synthesis of Enantioenriched α‑Chiral Bicyclo[1.1.1]pentanes

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journal contribution
posted on 2019-03-14, 19:43 authored by Marie L. J. Wong, James J. Mousseau, Steven J. Mansfield, Edward A. Anderson
Bicyclo­[1.1.1]­pentanes (BCPs), useful surrogates for para-substituted arenes, alkynes, and tert-butyl groups in medicinal chemistry, are challenging to prepare when featuring stereogenic centers adjacent to the BCP. We report the development of an efficient route to α-chiral BCPs, via highly diastereoselective asymmetric enolate functionalization. We also describe the application of this chemistry to the synthesis of BCP analogues of phenylglycine and tarenflurbil, the single enantiomer of the NSAID flurbiprofen.