Base‐Free Asymmetric Transfer Hydrogenation of 1,2‐Di‐ and Monoketones Catalyzed by a (NH) 2 P 2 ‐Macrocyclic Iron(II) Hydride | Zendy

De Luca Lorena | Zendy; Mezzetti Antonio | Zendy

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Base‐Free Asymmetric Transfer Hydrogenation of 1,2‐Di‐ and Monoketones Catalyzed by a (NH) 2 P 2 ‐Macrocyclic Iron(II) Hydride

Author(s) -

De Luca Lorena,

Mezzetti Antonio

Publication year - 2017

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201706261

Subject(s) - hydride , chemistry , catalysis , transfer hydrogenation , stereocenter , yield (engineering) , base (topology) , medicinal chemistry , noyori asymmetric hydrogenation , hydrogen , organic chemistry , enantioselective synthesis , ruthenium , materials science , mathematical analysis , mathematics , metallurgy

The hydride isonitrile complex [FeH(CNCEt 3 )( 1 a )]BF 4 ( 2 ) containing a chiral P 2 (NH) 2 macrocycle ( 1 a ), in the presence of 2‐propanol as hydrogen donor, catalyzes the base‐free asymmetric transfer hydrogenation (ATH) of prostereogenic ketones to alcohols and the hemihydrogenation of benzils to benzoins, which contain a base‐labile stereocenter. Benzoins are formed in up to 83 % isolated yield with enantioselectivity reaching 95 % ee. Ketones give the same enantioselectivity observed with the parent catalytic system [Fe(CNCEt 3 ) 2 ( 1 a )] ( 3 a ) that operates with added NaO t Bu.

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