Synfacts 2014; 10(1): 0067
DOI: 10.1055/s-0033-1340443
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Hydrogenation of Imines Using Cooperative Catalysis

Rezensent(en):
Mark Lautens
,
Zafar Qureshi
Tang W, Johnston S, Li C, Iggo JA, Bacsa J, Xiao J * University of Liverpool, UK
Cooperative Catalysis: Combining an Achiral Metal Catalyst with a Chiral Brønsted Acid Enables Highly Enantioselective Hydrogenation of Imines.

Chem. Eur. J. 2013;
19: 14187-14193
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Publikationsverlauf

Publikationsdatum:
13. Dezember 2013 (online)

 

Significance

Optically active amines are common in many fine chemicals, agrochemicals, and pharmaceuticals. The authors report a cooperative metal-organo catalytic system utilizing a chiral Brønsted acid and an achiral iridium catalyst (see below for a Review on transfer hydrogenation).


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Review

C. Zheng, S.-L. You Chem. Soc. Rev. 2012, 41, 2498–2518.


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Comment

The authors have reported the cooperative use of a chiral iridium catalyst with a chiral phosphoric acid in the asymmetric hydrogenation of acyclic imines with H2 (J. Am. Chem. Soc. 2008, 130, 14450). Here, they report an achiral iridium catalyst with a chiral phosphoric acid in a similar reaction. Alkyl imines, which are known to be difficult substrates for asymmetric hydrogenation, were shown to be excellent substrates in this system, giving enantioselectivities up to 97%.


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