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.
Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.
GRAPHICAL ABSTRACT
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.