Ruthenium-Catalyzed Asymmetric Hydrogenation of β-Keto- enamines: An Efficient Approach to Chiral γ-Amino Alcohols

✍ Scribed by Huiling Geng; Xiaowei Zhang; Mingxin Chang; Le Zhou; Wenjun Wu; Xumu Zhang

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 173 KB
• Volume: 353
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.201100305

✦ Synopsis

Abstract

A highly efficient and enantioselective hydrogenation of unprotected β‐ketoenamines catalyzed with ruthenium(II) dichloro{(S)‐(−)‐2,2′‐bis[di(3,5‐xylyl)phosphino]‐1,1′‐binaphthyl}[(2__S__)‐(+)‐1,1‐bis(4‐methoxyphenyl)‐3‐methyl‐1,2‐butanediamine] {Ru[(S)‐xylbinap][(S)‐daipen]Cl~2~} has been successfully developed. This methodology provides a straightforward access to free γ‐secondary amino alcohols, which are key building blocks for a variety of pharmaceuticals and natural products, with high yields (>99%) and excellent enantioselectivities (up to 99% ee) in all cases.