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Ruthenium‐Catalyzed Asymmetric Hydrogenation of β‐Keto‐ enamines: An Efficient Approach to Chiral γ‐Amino Alcohols
Author(s) -
Geng Huiling,
Zhang Xiaowei,
Chang Mingxin,
Zhou Le,
Wu Wenjun,
Zhang Xumu
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100305
Subject(s) - chemistry , ruthenium , enantioselective synthesis , catalysis , asymmetric hydrogenation , organic chemistry , noyori asymmetric hydrogenation , combinatorial chemistry , medicinal chemistry
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.
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