Modular synthesis of 2-furyl carbinols from 3-benzyldimethylsilylfurfural platforms relying on oxygen-assisted C–Si bond functionalization

• Sebastien Curpanen,
• Per Reichert,
• Gabriele Lupidi,
• Giovanni Poli,
• Julie Oble and
• Alejandro Perez-Luna

Beilstein J. Org. Chem. 2022, 18, 1256–1263, doi:10.3762/bjoc.18.131

• reactions from C3-silylated furfurals with triorganosilane units have failed so far. 2-Furyl carbinols represent a useful class of furanic synthetic intermediates that have given rise to a number of synthetically relevant transformations, such as the Piancatelli and aza-Piancatelli reactions [16][17] or the

Enantioselective PCCP Brønsted acid-catalyzed aza-Piancatelli rearrangement

• Gabrielle R. Hammersley,
• Meghan F. Nichol,
• Helena C. Steffens,
• Jose M. Delgado,
• Gesine K. Veits and
• Javier Read de Alaniz

Beilstein J. Org. Chem. 2019, 15, 1569–1574, doi:10.3762/bjoc.15.160

• Gabrielle R. Hammersley Meghan F. Nichol Helena C. Steffens Jose M. Delgado Gesine K. Veits Javier Read de Alaniz Department of Chemistry and Biochemistry, University of California Santa Barbara, Santa Barbara, CA 93106-9510, USA 10.3762/bjoc.15.160 Abstract An enantioselective aza-Piancatelli

• rearrangement has been developed using a chiral Brønsted acid based on pentacarboxycyclopentadiene (PCCP). This reaction provides rapid access to valuable chiral 4-amino-2-cyclopentenone building blocks from readily available starting material and is operationally simple. Keywords: aza-Piancatelli; Brønsted

• methodologies to construct this privileged scaffold. The aza-Piancatelli reaction has recently emerged as a particularly attractive method to access densely functionalized cyclopentene cores bearing nitrogen substituents directly from readily available 2-furylcarbinols [13][14][15]. Inspired by Piancatelli’s