Abstract
A four-step synthesis of sterically demanding (R)-phenanthren-9-yl-[(S)-pyrrolidin-2-yl] methanol has been easily accomplished starting from L-proline in high diastereoselectivity. These compounds are potentially useful ligands in metal-catalyzed reactions and organocatalysts.
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GRAPHICAL ABSTRACT
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ACKNOWLEDGMENTS
Ministero Italiano dell'Università e Ricerca Scientifica e Tecnologica (MIUR) is gratefully acknowledged for financial support. R. Zanasi is thanked for helpful suggestions in DFT calculations. P. Iannece is thanked for mass spectra and elemental analyses.
Notes
a Overall yield of compound 8 after two steps.
b The diastereoisomeric ratio was determined by Citation 1 H NMR analysis.