Ru-Catalyzed Asymmetric Hydrogenation of Racemic Aldehydes via Dynamic Kinetic Resolution:  Efficient Synthesis of Optically Active Primary Alcohols

Xie, Jian‐Hua; Zhou, Zhangtao; Kong, Weiling; Zhou, Qi‐Lin

doi:10.1021/ja0680109

Cited by 102 publications

(37 citation statements)

References 22 publications

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“…[36] Interestingly,t his is at ransformation that may also be conducted with ar uthenium catalyst in the presence of chiral ligands 29 and 30. [37] Thec hemo-and biocatalytic approaches are coeval in their development. Both underscore how methods development, regardless of its origins,i mpacts the retrosynthetic analysis and strategy selection.…”

Section: Deracemizing Reductase Activitymentioning

confidence: 99%

Enantioselective Chemo‐ and Biocatalysis: Partners in Retrosynthesis

et al. 2017

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Recent developments of stereoselective biocatalytic and chemocatalytic methods are discussed. The review provides a guide to the use of biocatalytic methods in the area of chemical synthesis with focused attention on retrosynthetic considerations and analysis. The transformations presented are organized according to bond disconnections and attendant synthetic methods. The review is expected to lead to better understanding of the characteristics and distinctions of the two complementary approaches. It depicts for researchers in bio- and chemocatalysis a road map of challenges and opportunities for the evolution (and at times revolution) in chemical synthesis.

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Section: Deracemizing Reductase Activitymentioning

confidence: 99%

Enantioselective Chemo‐ and Biocatalysis: Partners in Retrosynthesis

et al. 2017

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“…For example, the Ru complexes of BICP type of ligands 22 and 23 combined with nonchiral 2 -(alkylthio)amine or 1,2 -diamine have shown good performances for the highly enantioselective hydrogenation of aryl ketones in the presence of alkoxides as the base [276] . Zhou and others reported a highly effi cient dynamic kinetic resolution via asymmetric hydrogenation of aryl aldehyde [304,305] . A series of chiral primary alcohols were prepared in high selectivities using a Ru -SDP catalyst.…”

Section: Aromatic Ketonesmentioning

confidence: 99%

Transition Metal‐Catalyzed Homogeneous Asymmetric Hydrogenation

Gao

Zhang

2010

Catalytic Asymmetric Synthesis

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INTRODUCTIONAmong all the catalytic asymmetric methodologies to chiral compounds, homogenous transition metal -catalyzed asymmetric hydrogenation plays a particularly important role [1] . Its highly effi cient, environmental friendly, and cost -effective natures have undoubtly made it one of the most studied methodologies during the past 40 years. As a result, the vast number of catalytic systems developed has also had a signifi cant impact on other areas of asymmetric catalysis [2] . More signifi cantly, the achievements from academia research on asymmetric hydrogenation were frequently acknowledged with industrial applications, which, in turn, provide an important driving force for its basic research [3] .Hundreds of catalytic systems have been developed since the seminal discoveries from Knowles and Sabacky [4] , Kagan and Dang [5] , and Horner et al. [6] . In many cases, series of chiral catalysts were developed based on the similar scaffolds and were prepared for the same reactions. Although these analogous ligands are more likely prepared for the purpose of patent protection other than academic curiosity, they indeed provide us an excellent opportunity to compare, evaluate, and study every aspect of the catalysts in asymmetric hydrogenation. In the meantime, a large number of prochiral unsaturated compounds have been successfully hydrogenated with excellent enantioselectivities. Practical applications with very low catalyst loadings and complex substrate structures have continued to emerge since the publication of the last edition of this book.

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“…It was obvious that eroding of optical purity was caused by the base-catalyzed racemization of the plausible intermediate aldehyde (Scheme 1). [10,13] In the case of unprotected b-amino and b-hydroxy esters, no products were obtained (entries 3 and 4). In entry 3, a b-amino ester disappeared because of its instability under basic condition.…”

Section: Hydrogenation Of Chiral Estersmentioning

confidence: 99%