Catalytic Hydrogenation of N‐protected α‐Amino Acids Using Ruthenium Complexes with Monodentate Phosphine Ligands. Issue 2 (22nd November 2019)

• Record Type: Journal Article
• Authors: Saito, Akari; Yoshioka, Shota; Naruto, Masayuki; Saito, Susumu
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 2(2020)
• Page Start: 424
• Page End: 429
• Publication Date: 2019-11-22
• Subjects: α-Amino acid -- Hydrogenation -- Ruthenium complex -- Monodentate phosphine -- β-Amino alcohol; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201901298
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A ruthenium complex with a monodentate phosphine ligand was used to catalytically hydrogenate N‐protected α‐amino acids under essential retention of the configuration of their α‐chiral centers. Among the ligands tested for this hydrogenation, which proceeds at a relatively low temperature, tris( para ‐fluorophenyl)phosphine exhibited the best performance. In comparison, electron‐rich monodentate, bidentate, and tridentate phosphines were far less effective. The precatalyst Ru(OAc)2 [( p ‐FC6 H4 )3 P]2 was synthesized and isolated, and its structure was determined by a single‐crystal X‐ray diffraction analysis. N‐protected α‐amino acids with neutral alkyl side chains, including polar functional groups such as sulfides, indoles, ethers, phenols, pyrroles, and arenes, are compatible with the applied hydrogenation conditions, affording the corresponding optically active 2‐substituted‐2‐(1 H ‐pyrrol‐1‐yl)ethan‐1‐ol (2‐amino ethanol) derivatives in moderate to high yield. Abstract :