Solvent and in situ catalyst preparation impacts upon Noyori reductions of aryl-chloromethyl ketones: application to syntheses of chiral 2-amino-1-aryl-ethanols

Tanis, Steven P.; Evans, Bruce R.; Nieman, James A.; Parker, Timothy T.; Taylor, Wayne E.; Heasley, Steven E.; Herrinton, Paul M.; Perrault, William R.; Hohler, Richard A.; Dolak, Lester A.; Hester, Matthew R.; Seest, Eric P.

doi:10.1016/j.tetasy.2006.07.017

Cited by 41 publications

(27 citation statements)

References 57 publications

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“…The spectroscopy data ( 1 H-NMR, MS and IR) of 2 were in agreement with those reported in the literature (Tanis et al 2006). …”

Section: Synthesis Of Racemicsupporting

confidence: 90%

“…-17.08°(ca. 3.2, CHCl 3 ; 50% ee), with that reported in the literature (De Carvalho et al 1991;Tanis et al 2006). On this basis the reduction product was determined to be (S)-(-)-a-chlorophenylethanol.…”

Section: Resultssupporting

confidence: 72%

“…The absolute configuration of the product was determined by comparison of the sign of the measured specific rotation with that reported in the literature (De Carvalho et al 1991;Tanis et al 2006).…”

Section: Assignment Of the Absolute Configuration Ofmentioning

confidence: 99%

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Bioreduction of α-chloroacetophenone by whole cells of marine fungi

et al. 2009

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The asymmetric reduction of 2-chloro-1-phenylethanone (1) by seven strains of marine fungi was evaluated and afforded (S)-(-)-2-chloro-1-phenylethanol with, in the best case, an enantiomeric excess of 50% and an isolated yield of 60%. The ability of marine fungi to catalyse the reduction was directly dependent on growth in artificial sea water-based medium containing a high concentration of Cl(-) (1.2 M). When fungi were grown in the absence of artificial sea water, no reduction of 1 by whole cells was observed. The biocatalytic reduction of 1 was more efficient at neutral rather than acidic pH values and in the absence of glucose as co-substrate.

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“…The spectroscopy data ( 1 H-NMR, MS and IR) of 2 were in agreement with those reported in the literature (Tanis et al 2006). …”

Section: Synthesis Of Racemicsupporting

confidence: 90%

Section: Resultssupporting

confidence: 72%

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Bioreduction of α-chloroacetophenone by whole cells of marine fungi

et al. 2009

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“…[1][2][3][4] In fact, they provide prochiral building blocks for synthesizing enantiopure aziridines, [5] halohydrins, [6][7][8] or aminoalkyl epoxides, [9][10][11] as well as substrates for cross-coupling reactions with organometallic enolates. [12] Furthermore, the biological activity of achloromethyl ketones as enzyme inhibitors has been described, [13,14] as has their use as affinity labelling agents.…”

mentioning

confidence: 99%

Highly Efficient Synthesis of New α‐Arylamino‐α′‐chloropropan‐2‐ones via Oxidative Hydrolysis of Vinyl Chlorides Promoted by Calcium Hypochlorite

Pace¹,

Martı́nez²,

Fernandez³

et al. 2009

Adv Synth Catal

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Abstract:The oxidative hydrolysis of different trifluoroacetyl-protected N-(2-chloroallyl)anilines, promoted by calcium hypochlorite, is able to yield several not previously described a-arylamino-a'-chloropropan-2-ones, very valuable building blocks that are useful as precursors of several drugs, in excellent yields and short reaction times. The main requirement of the reaction for avoiding the undesired aromatic chlorination (N-protection) is effectively solved by the use of the easily formed and removed N-trifluoroacetyl group. Thus, it is possible to perform the oxidative hydrolysis-deprotection step using a one-pot strategy, obtaining quantitative yields in very short reaction times.

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“…For related literature, see: Arıcı et al (2004); Bachechi et al (1988); Fothergill et al (1977); Gareth (2001); Ocak Ískeleli et al (2005); Narimatsu et al (2003); Tanis et al (2006); Thiruvalluvar et al (2003); Weerawarna et al (1991); Zaidlewicz et al (2005).…”

Section: Related Literaturementioning

confidence: 99%

1-(1-Benzofuran-2-yl)-2-chloroethanone

2007

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Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.004 Å; R factor = 0.086; wR factor = 0.165; data-to-parameter ratio = 23.1.The title compound, C 10 H 7 ClO 2 , was synthesized from 1-benzofuran-2-ylethanone by chlorination with thionyl chloride. The benzofuran ring system and the carbonyl group are coplanar. The carbonyl group is in a syn position relative to both the O atom of the benzofuran ring and the Cl atom. C-HÁ Á ÁO contacts are found between the methylene group and carbonyl O atom. Molecules related by a centre of symmetry are involved ininteractions, with distances between the centroids of the furan rings of 3.785 (3) Å .

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Solvent and in situ catalyst preparation impacts upon Noyori reductions of aryl-chloromethyl ketones: application to syntheses of chiral 2-amino-1-aryl-ethanols

Cited by 41 publications

References 57 publications

Bioreduction of α-chloroacetophenone by whole cells of marine fungi

Bioreduction of α-chloroacetophenone by whole cells of marine fungi

Highly Efficient Synthesis of New α‐Arylamino‐α′‐chloropropan‐2‐ones via Oxidative Hydrolysis of Vinyl Chlorides Promoted by Calcium Hypochlorite

1-(1-Benzofuran-2-yl)-2-chloroethanone

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