Diastereoselective Synthesis of (R)-Phenanthrenyl-9yl-[(S)-pyrrolidin-2yl)] Methanol

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

Keywords:

• β-Amino alcohols
• diastereoselective synthesis
• L-proline derivatives

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 ¹ H NMR analysis.