(1S,3R,4R)-2-Azanorbornylmethanol, an Efficient Ligand for Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of Ketones

Alonso, Diego A.; Guijarro, David; Pinho, Pedro; Temme, Oliver; Andersson, Pher G.

doi:10.1021/jo972082o

Cited by 135 publications

(27 citation statements)

References 33 publications

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“…28 12 can be used as a chiral ligand for asymmetric transfer hydrogenation of ketones, 28 and as a starting material for ring-closure reactions. 19,20 The synthesis of heterocycle 14 started from the pchlorophenyl isothiocyanate adduct of 12.…”

Section: Methodsmentioning

confidence: 99%

Ring closure reactions of bicyclic prolinol and prolin ester enantiomers

Palkó¹,

Molnár²,

Kivelä³

et al. 2009

Arkivoc

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Starting from the of bicyclic proline ester, ethyl exo-2-azabicyclo[2.2.1]heptane-3-carboxylate (+)-5 several hydantoines and thiohydantoines were prepared by acidic ring closure of the corresponding urea or thiourea derivatives. Enantiomer (-)-5 was reduced to 2-azanorbornylmethanol 12, which was transformed to 5,8-methanooxazolo-and thiazolo[3,4-a]pyridine derivatives. The structures, stereochemistry and relative configurations of the synthesized compounds were proved by NMR.

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Section: Methodsmentioning

confidence: 99%

Ring closure reactions of bicyclic prolinol and prolin ester enantiomers

Palkó¹,

Molnár²,

Kivelä³

et al. 2009

Arkivoc

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“…Andersson et al [21][22][23][24][25] have successfully developed 2-Azanorboronyl based amino alcohols as ligands and used in the Ru(II) catalyzed asymmetric transfer hydrogenation of aryl alkyl ketones like acetophenone. Asymmetric Electronic supplementary material The online version of this article (doi:10.1007/s10562-010-0408-y) contains supplementary material, which is available to authorized users.…”

Section: Introductionmentioning

confidence: 98%

Catalytic Asymmetric Transfer Hydrogenation of Ketones Using [Ru(p-cymene)Cl2]2 with Chiral Amino Alcohol Ligands

et al. 2010

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“…A number of enantiomerically pure 1,2-amino alcohols were found to act as efficient ligands in the transformation, but the ruthenium-arene complex of TsDPEN remains as one of the best catalysts for the reduction of ketones. [7] Apart from diamine-based ligands, Zhang and co-workers introduced chiral tridentate bis-oxazoline ligands which, upon complexation with ruthenium salts, resulted in highly active and enantioselective catalysts for the reduction of aryl alkyl ketones. [8] Inspired by the results obtained by Zhang, we investigated the catalytic ability of a number of ruthenium complexes based on N-functionalized 2-aminomethyloxazoline derivatives.…”

Section: Introductionmentioning

confidence: 99%