Enantioselective reduction of aromatic ketones catalysed by chiral ruthenium(II) complexes

Aitali, Mustapha; Allaoud, S.; Karim, Abdellah; Méliet, Catherine; Mortreux, André

doi:10.1016/s0957-4166(00)00055-0

Cited by 39 publications

(14 citation statements)

References 31 publications

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“…37 An evaluation of the optical purity of both unconverted 4a-c and the produced 6a-c showed, at all Scheme 1. Retrosynthetic analysis of C5-substituted indolizidines.…”

Section: Synthesis Of 56-dihydroindolizines From N-allylpyrroles Viamentioning

confidence: 99%

Synthesis of indolizidines from optically pure α‐amino acids via stereocontrolled rhodium‐catalyzed hydroformylation of N‐allylpyrroles

Lazzaroni

Settambolo

2011

Chirality

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Indolizidine alkaloids have attracted considerable attention because of their vast array of structural diversity and varied biological activity. This article relates the results that we obtained in the field of the total synthesis of indolizidines from α-amino acids, based on the rhodium-catalyzed hydroformylation of N-allylpyrroles intermediates. The formed pyrrolylbutanals undergo an intramolecular cyclodehydration to 5,6-dihydroindolizines, which are fully hydrogenated to indolizidines. All reaction sequences are stereocontrolled: indeed, the chiral center in the starting amino acid is transferred into 5,6-dihydroindolizine moiety with complete stereochemical integrity and the new stereogenic center at C9 carbon atom in the final indolizidines is generated in only one configuration.

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“…37 An evaluation of the optical purity of both unconverted 4a-c and the produced 6a-c showed, at all Scheme 1. Retrosynthetic analysis of C5-substituted indolizidines.…”

Section: Synthesis Of 56-dihydroindolizines From N-allylpyrroles Viamentioning

confidence: 99%

Synthesis of indolizidines from optically pure α‐amino acids via stereocontrolled rhodium‐catalyzed hydroformylation of N‐allylpyrroles

Lazzaroni

Settambolo

2011

Chirality

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“…27 Additionally, a ruthenium(II) complex prepared from [Ru(pcymene)Cl 2 ] 2 and (S)-AMP selectively reduces acetophenone in the presence of sodium isopropoxide in excellent yield (93%) and high ee (89%). 28 However, poor enantioselectivities (8%) were achieved in the reduction of acetophenone with ZnEt 2 and polymethylhydrosiloxane in the presence of (S)-AMP. 29…”

Section: Ohmentioning

confidence: 99%

(S)-2-(Anilinomethyl)pyrrolidine

Soai

Frederick

Crucho

et al. 2016

Encyclopedia of Reagents for Organic Synthesis

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“…Karim studied the complexation of [Ru(p-Cy)Cl 2 ] 2 with chiral diamines and β-amino alcohols, such as 115-119, and demonstrated that the complexes with diamines 118 and 119 can afford good enantioselectivities (up to 89-95%ee) in hydrogenations of acetophenone [81]. The ligands 115, 116 and 117 only induced 51%, 51% and 78%, respectively.…”

Section: Transfer Hydrogenationsmentioning

confidence: 99%

Recently Developed Organometallic Complexes of Zn, Cu(Zn, Li), Fe, Ru and Less-used Ions. Use in Selective 1,2-or 1,4-Additions, Transfer Hydrogenations, Aldol Reactions and Diels-Alder Reactions

Zhu¹,

Jiang

Ren

et al. 2005

COS

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This review introduces the broad general topic of asymmetric organic synthetic reactions and reagents. Reagents containing both frequently used metallic ions, e.g. Zn ++ , Cu +(++) and Ru ++ , and rarely used ions, such as Ag + , employed in the construction of designed chiral centers, are updated here. Enantioselective 1,2-additions and 1,4-conjugate additions, transfer hydrogenations, and diasteroselective aldol reaction are discussed. The selectivities induced by chiral β-, δor γ-chiral amino alcohols, chiral diols, chiral binaphthyl derivatives, chiral P,N-containing auxiliaries, and other ligands used to prepare chiral metallic complexes, were compared in each reaction system. The use of two or more metallic ions with a single chiral ligand has now become a more popular strategy to catalyze chiral-center-controlled processes. For example, only diethylzinc was used in enantioselective additions to aldehydes in early studies. Recently, the combination of Et 2 Zn and Cu ++ in the selective additions has been used to achieve high ee% values and yields. Finally, quantum calculations have been used to obtain kinetic data to predict a reactions ee% values. For example, the calculated ∆G cal. values have a strong relationship with the obtained ∆G fit values which have the direct linkage with the ee% values. EntryActivator ee (%) at 0 °°°°C (config.) ee (%) at -45 °°°°C (config.)

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Enantioselective reduction of aromatic ketones catalysed by chiral ruthenium(II) complexes

Cited by 39 publications

References 31 publications

Synthesis of indolizidines from optically pure α‐amino acids via stereocontrolled rhodium‐catalyzed hydroformylation of N‐allylpyrroles

Synthesis of indolizidines from optically pure α‐amino acids via stereocontrolled rhodium‐catalyzed hydroformylation of N‐allylpyrroles

(S)-2-(Anilinomethyl)pyrrolidine

Recently Developed Organometallic Complexes of Zn, Cu(Zn, Li), Fe, Ru and Less-used Ions. Use in Selective 1,2-or 1,4-Additions, Transfer Hydrogenations, Aldol Reactions and Diels-Alder Reactions

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