Jackson reagent

SCHEME 7. Ultrasound-mediated preparation of the Jackson reagent 15 and its uses... 

The preparation of alkylzinc iodides is facilitated if the reaction is performed in THF and NMP mixtures. Such solutions of Me02C(CH2)4ZnI add to benzaldehyde in the presence of TMSCI (2 equiv.) in 70% yield.33 The use of ultrasound also promotes the formation of organozinc compounds.34>34a 34e This procedure proved to be especially useful for the preparation of Jackson reagent 6 derived from serine. In the presence of a copper(l) or palladium(O) catalyst, this zinc derivative reacts with various electrophiles (Scheme 1) 3S,3Sa-3Sj 0f z nc reagent 7 leading to methyl but-3-enoate and the zinc amide... 

We have found that the LC-MS/MS system performs better with Burdick 8c Jackson reagents. The cleaner the mobile phase used, the less the instrument becomes dirty during a run, ensuring a uniform analysis from start to finish. 

Synthesis of a protected non-natural amino acid 233 using the Jackson reagent 23(P ... 

Jackson and coworkers have used a new approach to the synthesis of fi-hydtoxy-ct-amino acids using farylthio nitrooxiranes. c-Jsopropylideneglyceraldehyde is converted into the corresponding 1-arylthio-l-nitroalkene, which is a key material for stereoselective synthesis of fi,Y-dihydroxyamino acids fScheme 4.6. The key step is stereoselective nucleophilic epoxlda-donof the Tarylthio-Tnltroalkene. Sy)i and ruin epoxides are selecdvely obtained by appropriate choice of epoxidadon reagent." ... 

Materials. All solvents were "Distilled in Glass" from Burdick and Jackson (Muskegon, MI). All other reagents were ACS grade, except where otherwise noted. Celite 560 (Johns Manville, Lompoc, CA) was screened to remove particles smaller than 60 mesh and used without further treatment. 

This work and SGC were supported by a Wellcome Trust project grant 080349/Z/06/Z to MPA. We thank G. Pereira and G. Pavitt for reagents and D. Jackson and C. Tang for their assistance with the confocal microscopy. 

Storer RI, Takemoto T, Jackson PS, Ley SV (2003) A total synthesis of epo-thilones using solid-supported reagents and scavengers. Angew Chem Int Ed 42 2521-2525... 

Materials. Aldicarb standards were obtained from the United States Environmental Protection Agency (USEPA), Quality Assurance Section and from Union Carbide Corporation. Crystalline samples of carbofuran and 3-hydroxycarbofuran were supplied by the Agricultural Chemical Group of FMC Corporation. Reference standards of methomyl (99% pure) and oxamyl (99% pure) were obtained from USEPA. HPLC grade methanol was purchased from Burdick and Jackson, Inc. Methylene chloride used for bulk extractions of the carbamate pesticides in solution was recovered, distilled and reused. Analytical reagent grade chemicals and solvents were used in all experiments. Doubly distilled deionized water was used for solution rate studies. Deionized distilled water (DDW) was used for dilutions in reactive ion exchange experim ts., , ... 

Ley SV, Baxendale IR, Bream RN, Jackson PS, Leach AG, Longbottom DA, Nesi M, Scott JS, Storer RI, Taylor SJ (2000) J Chem Soc Perkin Trans 1 3815-4193 45. Ley SV, Norman J (1995) In Paquette LA (ed) Encyclopedia of reagents for organic synthesis, vol 7. Wiley, Chichester, pp 4827 830 Bloch R, Brillet C (1991) Synlett 829-830 Hitchcock SA, Pattenden G (1992) Tetrahedron Lett 33 4843-4846 RyaU RP, Silverman RB (1990) Synth Commun 20 431-438... 

In 1997, Dunn and Jackson reported on a new approach to the synthesis of di- and tripeptides with unnatural amino acids by converting di- and tripeptides into organozinc reagents and coupling them with aryl iodides or acyl chlorides in the presence of Pd2(dba)3 and either PPhs or P(o-tol)3 under mild reaction conditions, with no loss of optical purity. " The synthesis of jS- and y-amino acids in an analogous fashion was reported shortly after (Scheme 12). " ... 

The work described here was performed in a laboratory which had been specially modified and equipped to handle chemical carcinogens (10). Strict care was taken to avoid worker exposure to hazardous chemicals during the course of these studies. Reagent grade chemicals used for this work were 1,2-dichloroethane (Alfa Products, Danvers, MA) 1,1,1-trichloroethane (Matheson, Coleman Bell, Norwood, OH) 1,1,2-trichloroethane (J.T. Baker Chemical Co., Phillipsburg, NJ) n-heptane and n-hexane (Burdick Si Jackson Laboratories, Inc., Muskegon, MI). Also,used was a polychlorinated biphenyl whose chemical composition as determined... 

Beil 1.601.(326) [668-70] 2JH.A.Iddles C.E.Jackson, AnalChem 6,454-6(1936) (Precipitation of acetaldehyde as hydrazone using 2,4-dinitrophenylhydrazine as a reagent) 3)Kirk Othmer l(1947),38(Qualitative and quantitative methods of determining acetaldehyde) 4)Jacobs(1949),476—8(Qualitative and quantitative methods of detn 5 Ullmanu 3 0953),11... 

Reagents. NaCl (Spectrum Chemical Co.) was fired 4 h at 550 °C in a muffle furnace to remove trace organic contaminants. Acetonitrile (HPLC grade J. T. Baker), dichloromethane (Burdick and Jackson), 5-dimethylamino-l-naphthalenesulfonyl chloride (dansyl chloride Aldrich), O-p-nitrobenzyl-N,N -diisopropylisourea (PNBDI Regis), and N-succinimidyl-p-nitrophenyl acetate (SNPA Regis) were used as purchased. 

Ley, S.V., Baxendale, I.R., Bream, R.N., Jackson, P.S., Leach, A.G. etal, Multi-step organic synthesis using solid-supported reagents and scavengers a new paradigm in chemical library generation, J. Chem. Soc, Perkin Trans. 1, 2000, 3815. 

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