2012
DOI: 10.1039/c2cs15312b
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Asymmetric homogeneous hydrogenations at scale

Abstract: Asymmetric hydrogenations are increasingly being used to introduce stereogenic centres into products used in the life sciences industries. There are a number of potential pitfalls when moving from a laboratory reaction to a manufacturing process, not least of which is safety. Time-to-market pressure leads to short development times, which in the past could be a large barrier for the implementation of catalytic steps; now there are new ways to minimise this problem. The potential problems associated with impuri… Show more

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Cited by 353 publications
(146 citation statements)
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References 333 publications
(435 reference statements)
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“…Asymmetric hydrogenation has been the major approacht ot his reduction since 1987, when the first success using Ru(OCOCH 3 ) 2 (binap) (binap = 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) was reported. [2,3] Two years later,P faltz and co-workers reported an excellent chiral Co semicorrin catalyst affecting asymmetric 1,4-reduction of a,b-unsaturated carboxylic esters by NaBH 4 ; [4] however,t his development did not result in as ignificant advance in the field. [5] This may be due to the lower atom efficiency,a sw ell as the higher Ef actor,o fN aBH 4 compared with that of the H 2 system.…”
mentioning
confidence: 99%
“…Asymmetric hydrogenation has been the major approacht ot his reduction since 1987, when the first success using Ru(OCOCH 3 ) 2 (binap) (binap = 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) was reported. [2,3] Two years later,P faltz and co-workers reported an excellent chiral Co semicorrin catalyst affecting asymmetric 1,4-reduction of a,b-unsaturated carboxylic esters by NaBH 4 ; [4] however,t his development did not result in as ignificant advance in the field. [5] This may be due to the lower atom efficiency,a sw ell as the higher Ef actor,o fN aBH 4 compared with that of the H 2 system.…”
mentioning
confidence: 99%
“…[ 1 , 2 ] A well-known example is the enantioselective iridium-catalysed hydrogenation leading to the synthesis of the herbicide (S)-metolachlor, representing one of the largest scale hydrogenations employed industrially. [2] A similarly well-known example is the first industrially implemented protocol for L-DOPA synthesis, which involved a rhodiumdiphosphine-catalysed hydrogenation step. [2] The majority of catalysts employed in asymmetric hydrogenation reactions are based on precious metals such as rhodium, [1] iridium, [ 3 ] and ruthenium.…”
Section: Introductionmentioning
confidence: 99%
“…[2] A similarly well-known example is the first industrially implemented protocol for L-DOPA synthesis, which involved a rhodiumdiphosphine-catalysed hydrogenation step. [2] The majority of catalysts employed in asymmetric hydrogenation reactions are based on precious metals such as rhodium, [1] iridium, [ 3 ] and ruthenium. [ 4 ] The cost of precious metals has fuelled academic and industrial research into alternative hydrogenation catalysts involving abundant base metals such as cobalt and iron.…”
Section: Introductionmentioning
confidence: 99%
“…205 Comparison with literature precedent or experimental screening is usually used to determine which type of catalyst system is to be used in a specific application. Many catalysts, when first developed, are tried with 'standard' substrates.…”
Section: Chiral Catalystsmentioning
confidence: 99%