Light-induced enantioselective hydrogenation using chiral derivatives of Casey’s iron-cyclopentadienone catalyst was written by Berkessel, Albrecht;Reichau, Sebastian;von der Hoeh, Adrian;Leconte, Nicolas;Neudorfl, Joerg-M.. And the article was included in Organometallics in 2011.Application In Synthesis of (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol This article mentions the following:
Iron cyclopentadienone half-sandwich complexes I [8a–e; R = H, Me, Ph, 2-naphthyl, 3,5-(CF3)2C6H3] and an (R)-enantiomer of 8a, ent-8a, containing chiral (S)- and (R)-MonoPhos ligands, chirally modified Casey’s catalysts, were prepared by Me3NO- or photolysis-induced substitution of the parent tricarbonyl complex, [[η4-O(CH2)2(C:CSiMe3)2C:O]Fe(CO)3] (7) with the chiral phosphoramidite ligands. Crystal structures of 8a and 8c were determined The complexes 8a–e and ent-8a catalyze asym. hydrogenation of acetophenone into (S)- and (R)-1-phenylethanol, resp., with 90% yields and up to 32% ee, the reaction being induced by UV irradiation Photolysis was also used to convert the dicarbonyl phosphoramidite complexes 8 to the coordinatively unsaturated monocarbonyl complexes, which are intermediates in the catalytic cycle of ketone hydrogenation. Hydrogen uptake by the latter species affords the “loaded” diastereomeric hydrides [[η5-O(CH2)2(C:CSiMe3)2COH]Fe(CO)(L*)] [10, 11; L* = unsubstituted (S)-MonoPhos] and an achiral hydride [[η5-O(CH2)2(C:CSiMe3)2COH]Fe(CO)2] (6), as evidenced by 1H NMR spectroscopy. Thus, the preparation of sensitive iron hydrides by the typically low-yielding Hieber reaction could be avoided. Instead, the catalytic cycle is accessed from air-stable carbonyl precursors. In the hydridic form of the phosphoramidite-carbonyl catalysts, the iron atom itself becomes a stereocenter. NMR spectroscopy confirmed the generation of two hydride diastereomers. With the MonoPhos iron dicarbonyl complex, moderate enantioselectivity (up to 31% ee) was achieved in the hydrogenation of acetophenone. In the experiment, the researchers used many compounds, for example, (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol (cas: 863659-89-6Application In Synthesis of (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol).
(S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol (cas: 863659-89-6) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.Application In Synthesis of (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol
Referemce:
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