An Enantioselective Synthesis of (<i>S</i>)-(+)-3-Aminomethyl-5-methylhexanoic Acid via Asymmetric Hydrogenation

Burk, Mark J.; Koning, Pieter D. de; Grote, Todd M.; Hoekstra, Marvin S.; Hoge, Garrett; Jennings, Rex A.; Kissel, William S.; Le, Tung; Lennon, Ian C.; Mulhern, Thomas A.; Ramsden, James A.; Wade, Robert A.

doi:10.1021/jo034397b

Cited by 138 publications

(68 citation statements)

References 13 publications

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“…182 It is used for the treatment of neuropathic pain and epilepsy. In 2003, Ramsden and co-workers developed a concise enantioselective synthesis of pregabalin, 183 where for the installation of a single chirogenic center, an enantioselective hydrogenation has been used (Scheme 29.4). After hydrogenation of 3-cyano-5-methylhex-3-enoic acid salt 123 in methanol at 55 C using [(R,R)-(Me-DuPhos)Rh (COD)]BF 4 126 as a precatalyst, desired (S)-3-cyano-5-methylhexanoate 124 was obtained with high enantioselectivity (up to 96-97% ee).…”

Section: Rh-catalyzed Hydrogenation To Drug and Natural Product Synthmentioning

confidence: 99%

Stereoselective Hydrogenation ofCCBonds: Application to Drug and Natural Product Synthesis

Andrushko

2013

Stereoselective Synthesis of Drugs and Natural Products

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Asymmetric homogeneous hydrogenation is perhaps one of the most researched areas in homogeneous catalysis; thus, it is now used in numerous innovative applications in stereoselective syntheses of many chiral pharmaceutical and natural products. Metal complexes, derived from transition metals, like Rh, Ru, Ir, and so on, and chiral ligands (usually mono‐ or diphosphine ligands), are widely used as catalysts in asymmetric alkene hydrogenation as a result of their efficiency in the preparation of enantiopure compounds with excellent atom economy. This chapter provides many interesting examples of homogeneous enantio‐ and diastereoselective hydrogenation of CC bonds, highlighting the utility of these methods as useful synthetic tools for the construction of stereogenic centers in stereoselective drug and natural product syntheses.

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Section: Rh-catalyzed Hydrogenation To Drug and Natural Product Synthmentioning

confidence: 99%

Stereoselective Hydrogenation ofCCBonds: Application to Drug and Natural Product Synthesis

Andrushko

2013

Stereoselective Synthesis of Drugs and Natural Products

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“…7.12 ) [49] . An Rh -Me -DuPhos complex also provides high enantioselectivity (97.7% ee) although from high catalyst loading ( S / C = 100) [200] . An isomeric mixture ( E / Z = 19:1) of 4,4 ′ -diaryl -3 -butenoate has been successfully hydrogenated to produce a chiral intermediate for an antidepressant agent sertraline.…”

Section: Unsaturated Acids and Their Derivativesmentioning

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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“…Enantiomerically pure 3-methyl-(41) and 3-mercaptomethyl-g-amino acids (50) have been prepared by a novel route for the synthesis of optically pure b-substituted GABA derivatives (Scheme 14.13). (S)-Phenylethylamine was used as a chiral auxiliary of the radical precursor (S)-(48) for a 5-exo-trig radical cyclization as the strategy for the construction of the 4-substituted pyrrolidinones (49).…”

Section: B-substituted G-amino Acidsmentioning

confidence: 99%