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Ru‐catalyzed Asymmetric Hydrogenation of Aryl Ketones Using Tetrazole Derived NH 2 ‐hybrid Ligand
Author(s) -
Bie Fusheng,
Li Yuehui,
Cao Weiguo,
Sanboval Christian A.
Publication year - 2009
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201090000
Subject(s) - chemistry , tetrazole , moiety , ligand (biochemistry) , catalysis , asymmetric hydrogenation , aryl , combinatorial chemistry , binap , solvent , chiral ligand , medicinal chemistry , organic chemistry , enantioselective synthesis , receptor , biochemistry , alkyl
Readily available chiral hybrid NH 2 /tetrazole ligand [( S )‐TEA, 1 ] in combination with Ru‐BINAP or Ru‐DIOP complexes catalyzes the asymmetric hydrogenation of a number of simple ketones with moderate enantioselectivity (up to 72% ee ). The tetrazole functionality results in reversal of the typically observed chiral‐induction for related systems and allows for hydrogenation to be uncharacteristically conducted in (non‐protic) THF solvent. The observed catalyst performance is sensitive to the reaction conditions employed and the particular compounds involved. The origins of such features are considered to derive from the added functionality provided by the tetrazole moiety in 1 , which due to its modular nature provides a good basis for further development.