RSS-Feed abonnieren
DOI: 10.1055/s-0030-1259979
Lesser-Known Enabling Technologies for Organic Synthesis
Publikationsverlauf
Publikationsdatum:
30. März 2011 (online)
Abstract
In this review we summarize both new emerging technologies as well as some overlooked methods which are beneficial to organic synthesis chemists.
1 Introduction
2 Separation Methods
2.1 Low-Temperature Chromatography
2.2 Reflux Chromatography
2.3 Phase-Switching Methods
2.3.1 Affinity-Based Phase-Switching
2.3.1.1 Fluorous Tags
2.3.1.2 Acid-Base and Polarity Tags
2.3.1.3 Transition-Metal and Ligand Affinity Tags
2.3.1.4 Hydrogen-Bonding Interactions
2.3.1.5 Polyaromatic Affinity Tags
2.3.1.6 Crown Ether Tags
2.3.1.7 Redox-Switchable Tags
2.3.2 Reactive and Irreversible Tags
2.3.2.1 ‘Click’ Tags
2.3.2.2 Diels-Alder Tags
2.3.3 Phase-Switching Involving Precipitation
2.3.3.1 Precipitation by Polymerisation
2.3.3.2 Solubility-Switching
2.3.3.3 Temperature-Dependent Solubility
2.3.4 Size-Exclusion Tags
3 Synthesis Methods
3.1 Cooled Microwave Heating
3.2 Ball-Milling
3.3 Design of Experiments and Related Techniques
4 Conclusion
Key words
separation methods - synthesis methods - new enabling technologies
-
1a
Tswett MS. Ber. Dtsch. Bot. Ges. 1906, 316 -
1b
Tswett MS. Ber. Dtsch. Bot. Ges. 1906, 384 -
1c
Tswett MS. Proceedings of the Warsaw Society of Naturalists, Biology Section 1903, 14: 20 - 2
Clements RL. Science 1958, 128: 899 -
3a
Gant JR.Dolan JW.Snyder LR. J. Chromatogr. 1979, 185: 153 -
3b
Norden B.Jonas I. Inorg. Nucl. Chem. Lett. 1976, 12: 33 -
3c
Jonas I.Norden B. Nature 1975, 258: 597 -
3d
Sheikh SU.Touchstone JC. J. Chromatogr. 1988, 455: 327 -
3e
Henderson DE.O’Connor DJ. Adv. Chromatogr. 1984, 23: 65 -
3f
Teutenberg T. Anal. Chim. Acta 2009, 643: 1 -
3g
Henderson DE.O’Connor DJ.Kirby JF.Sears CP. J. Chromatogr. Sci. 1985, 23: 477 -
3h
Hsu HW.Davis DS.Wei CH.Yang WK. Anal. Biochem. 1976, 73: 513 -
3i
Jones BA. J. Liq. Chromatogr. Relat. Technol. 2004, 27: 1331 -
3j
Lerosen AL.Rivet CA. Anal. Chem. 1948, 20: 1093 -
3k
Maggs RJ. J. Chromatogr. Sci. 1969, 7: 145 -
3l
Yamasaki T.Sakai M.Kanamori T.Sogo M. Chromatographia 1986, 21: 478 -
3m
Collins FD.Shotlander VL. J. Lipid Res. 1960, 1: 352 -
3n
Liodakis S.Pappa A.Parissakis G. J. Chromatogr. Sci. 1989, 27: 149 -
3o
Scott RPW.Lawrence JG. J. Chromatogr. Sci. 1969, 7: 65 -
3p
Stahl E. Angew. Chem. Int. Ed. 1964, 3: 784 -
3q
Locke DC.Martire DE. Anal. Chem. 1967, 39: 921 -
3r
Bolliet D.Poole CF. Analyst 1998, 123: 295 -
3s
Hesse G.Engelhar H. J. Chromatogr. 1966, 21: 228 -
3t
Chang LT. Anal. Chem. 1953, 25: 1235 -
3u
Magalhaes AF.Magalhaes EG.Junior VN.Filho HFL. Phytochemistry 1989, 28: 2497 - 4
Henderson RF.Clayton MH. Anal. Biochem. 1976, 70: 440 -
5a
Sheikh SU.Touchstone JC. Anal. Chem. 1987, 59: 1472 -
5b
Touchstone JC.Sheikh SU. J. High Resolut. Chromatogr. & Chromatogr. Commun. 1986, 9: 464 -
5c
Sheikh SU.Touchstone JC. J. Liq. Chromatogr. 1987, 10: 2489 - 6
Balny C.Lepeuch C.Debey P. Anal. Biochem. 1975, 63: 321 -
7a
Ewing GD.Ley SV.Paquette LA. J. Am. Chem. Soc. 1978, 100: 2909 -
7b
Paquette LA.Ewing GD.Ley SV.Berk HC.Traynor SG. J. Org. Chem. 1978, 43: 4712 - 8
Annis GD.Ley SV.Self CR.Sivaramakrishnan R. J. Chem. Soc., Perkin Trans. 1 1981, 270 - 9 inventors; , Essex CB11 3AZ. Huber UK, Shire Hill, Saffron
Walden
- 10
Horak V.Foster FV.de Levie R.Jones JW.Svoronos P. Tetrahedron Lett. 1981, 22: 3577 - 11
Jones DW.Wife RL. J. Chem. Soc., Perkin Trans. 1 1974, 1 -
12a
Jones DW.Pomfret A. J. Chem. Soc., Chem. Commun. 1983, 703 -
12b
Jones DW.Pomfret A. J. Chem. Soc., Perkin Trans. 1 1991, 13 - 13
Escher A.Rutsch W.Neuenschwander M. Helv. Chim. Acta 1986, 69: 1644 - 14
Gupta RC.Larsen DS.Stoodley RJ.Slawin AMZ.Williams DJ. J. Chem. Soc., Perkin Trans. 1 1989, 739 -
15a
Denmark SE.Lee WS. Chem. Asian J. 2008, 3: 327 -
15b
Denmark SE.Lee WS. J. Org. Chem. 1994, 59: 707 - 16
Toltl NP.Leigh WJ. Organometallics 1996, 15: 2554 - 17
Williams AL.Srinivasan JM.Johnston JN. Org. Lett. 2006, 8: 6047 - 18
Zhao WL.Carreira EM. Org. Lett. 2006, 8: 99 - 19
Sellmann D.Jonk E.Reinecke HJ.Wurminghausen T. Fresenius Z. Anal. Chem. 1979, 294: 372 - 20
Bergman RG.Seidler PF.Wenzel TT. J. Am. Chem. Soc. 1985, 107: 4358 -
21a
Mobley TA.Schade C.Bergman RG. J. Am. Chem. Soc. 1995, 117: 7822 -
21b
Mobley TA.Schade C.Bergman RG. Organometallics 1998, 17: 3574 - 22
Egekeze JO.Danielski MC.Grinberg N.Smith GB.Sidler DR.Perpall HJ.Bicker GR.Tway PC. Anal. Chem. 1995, 67: 2292 - 23
LoBrutto R.Bereznitski Y.Novak TJ.DiMichele L.Pan L.Journet M.Kowal J.Grinberg N.
J. Chromatogr., A 2003, 995: 67 - 24
Dugave C.Demange L. Chem. Rev. 2003, 103: 2475 - 25
Melander WR.Jacobson J.Horváth C. J. Chromatogr., A 1982, 234: 269 - 26
Henderson DE.Horváth C. J. Chromatogr., A 1986, 368: 203 - 27
Jacobson J.Melander W.Vaisnys G.Horváth C. J. Phys. Chem. 1984, 88: 4536 -
28a
Bouabdallah S.Trabelsi H.Bouzouita K.Sabbah S. J. Biochem. Biophys. Meth. 2002, 54: 391 -
28b
Henderson DE.Mello JA. J. Chromatogr., A 1990, 499: 79 -
28c
Lebl M.Fang S.Hruby VJ. J. Chromatogr. A 1991, 586: 145 -
28d
Liberek B.Augustiniak J.Ciarkowski J.Plucinski K.Stachowiak K. J. Chromatogr. 1974, 95: 223 -
28e
Henderson DE.Saltzman SJ.Uden PC.Cheng Z. Polyhedron 1988, 7: 369 -
28f
Moriyasu M.Kato A.Hashimoto Y. J. Chromatogr. 1987, 400: 143 - 29
Melander WR.Lin HJ.Jacobson J.Horváth C.
J. Phys. Chem. 1984, 88: 4527 -
30a
Li L.Thompson R.Sowa JR.Clausen A.Dowling T. J. Chromatogr., A 2004, 1043: 171 -
30b
Trapp O. Anal. Chem. 2006, 78: 189 -
30c
Trapp, O.; Schoetz, G.; Schurig, V. Determination of enantiomerization barriers by dynamic and stopped-flow chromatographic methods, 2nd International Symposium on Biological Chirality, Szeged, Hungary, Aug 27-31, 2000, 403
-
30d
Wolf C. Chem. Soc. Rev. 2005, 34: 595 -
30e
Casarini D.Lunazzi L.Alcaro S.Gasparrini F.Villani C. J. Org. Chem. 1995, 60: 5515 - 31
Meier R.Fletschinger J. Angew. Chem. 1956, 68: 373 - 32
Dewar MJS.Dewar RBK.Gaibel ZLF. Org. Synth. 1966, 46: 65 - 33
Kauffman JM.Bjorkman CO. J. Chem. Educ. 1976, 53: 33 - 35
Kauffman JM. Synthesis 1999, 918 - 36
Kauffman JM. Synthesis 2001, 197 - 37
Faldt A.Pedersen MJ.Krogh TP.Hviid L.Christensen JB. Synth. Met. 1998, 94: 307 - 38
Goodbrand HB.Hu NX. J. Org. Chem. 1999, 64: 670 - 39
Froimowitz M.Gu YH.Dakin LA.Nagafuji PM.Kelley CJ.Parrish D.Deschamps JR.Janowsky A. J. Med. Chem. 2007, 50: 219 -
40a
Chatterjee K.Parker DH.Wurz P.Lykke KR.Gruen DM.Stock LM. J. Org. Chem. 1992, 57: 3253 -
40b
Khemani KC.Prato M.Wudl F. J. Org. Chem. 1992, 57: 3254 - 41
Scrivens WA.Bedworth PV.Tour JM. J. Am. Chem. Soc. 1992, 114: 7917 -
42a
Darwish AD.Kroto HW.Taylor R.Walton DRM. J. Chem. Soc., Chem. Commun. 1994, 15 -
42b
Grushko YS.Sedov VP.Shilin VA. Russ. J. Appl. Chem. 2007, 80: 448 - 43
O’Brien M.Dieguez-Vazquez A.Hsu DS.Kraus H.Sumino Y.Ley SV. Org. Biomol. Chem. 2008, 6: 1159 -
44a
Ball M.Gaunt MJ.Hook DF.Jessiman AS.Kawahara S.Orsini P.Scolaro A.Talbot AC.Tanner HR.Yamanoi S.Ley SV. Angew. Chem. Int. Ed. 2005, 44: 5433 -
44b
Gaunt MJ.Jessiman AS.Orsini P.Tanner HR.Hook DF.Ley SV. Org. Lett. 2003, 5: 4819 -
44c
Gaunt MJ.Hook DF.Tanner HR.Ley SV. Org. Lett. 2003, 5: 4815 - 45
Merrifield RB. J. Am. Chem. Soc. 1963, 85: 2149 - 46
Linclau B.Sing AK.Curran DP. J. Org. Chem. 1999, 64: 2835 - 47
Flynn DL. Med. Res. Rev. 1999, 19: 408 -
48a
Zhu DW. Synthesis 1993, 953 -
48b
Curran DP.Hadida S. J. Am. Chem. Soc. 1996, 118: 2531 -
48c
Studer A.Hadida S.Ferritto R.Kim SY.Jeger P.Wipf P.Curran DP. Science 1997, 275: 823 -
48d
Horvath IT.Rabai J. Science 1994, 266: 72 -
49a
Curran DP. Angew. Chem. Int. Ed. 1998, 37: 1175 -
49b
Gladysz JA.Curran DP.Horvath IT. Handbook of Fluorous Chemistry Wiley-VCH; Weinheim: 2004. -
49c
Zhang W. Chem. Rev. 2004, 104: 2531 -
49d
Horvath IT. Acc. Chem. Res. 1998, 31: 641 -
49e
de Wolf E.van Koten G.Deelman BJ. Chem. Soc. Rev. 1999, 28: 37 - 50
McAllister LA.McCormick RA.Brand S.Procter DJ. Angew. Chem. Int. Ed. 2005, 44: 452 -
51a
Sheehan JC.Hlavka JJ. J. Org. Chem. 1956, 21: 439 -
51b
Sheehan JC.Boshart GL.Cruickshank PA. J. Org. Chem. 1961, 26: 2525 - 52
Camp D.Jenkins ID. Aust. J. Chem. 1988, 41: 1835 -
53a
El Bakkari M.Vincent JM. QSAR Comb. Sci. 2006, 25: 689 -
53b
Yoshida J.Itami K.Mitsudo K.Suga S. Tetrahedron Lett. 1999, 40: 3403 - 54
Sugimura T.Hagiya K. Chem. Lett. 2007, 36: 566 - 55
Flynn DL.Crich JZ.Devraj RV.Hockerman SL.Parlow JJ.South MS.Woodard S. J. Am. Chem. Soc. 1997, 119: 4874 - 56
Smith CD.Baxendale IR.Tranmer GK.Baumann M.Smith SC.Lewthwaite RA.Ley SV. Org. Biomol. Chem. 2007, 5: 1562 - 57
Kunst E.Gallier F.Dujardin G.Yusubov MS.Kirschning A. Org. Lett. 2007, 9: 5199 - 58
Mothana S.Chahal N.Vanneste S.Hall DG. J. Comb. Chem. 2007, 9: 193 - 59
Ley SV.Massi A.Rodriguez F.Horwell DC.Lewthwaite RA.Pritchard MC.Reid AM. Angew. Chem. Int. Ed. 2001, 40: 1053 - 60
Siu J.Baxendale IR.Lewthwaite RA.Ley SV. Org. Biomol. Chem. 2005, 3: 3140 - 61
El Bakkari M.Fronton B.Luguya R.Vincent J.-M. J. Fluorine Chem. 2006, 127: 558 - 62
Fersht AR. Trends Biochem. Sci. 1987, 12: 301 - 63
Gruijters BWT.Verkade JMM.van Delft FL.Sijbesma RP.Hermkens PHH.Rutjes F. Eur. J. Org. Chem. 2007, 4197 - 64
Zhang SQ.Fukase K.Izumi M.Fukase Y.Kusumoto S. Synlett 2001, 590 - 65
de Ridder DJ.Villacorte L.Verliefde ARD.Verberk JQJC.Heijman SGJ.Amy GL.van Dijk JC. Water Res. 2010, 44: 3077 - 66
Hay AM.Hobbs-Dewitt S.MacDonald AA.Ramage R. Synthesis 1999, 1979 - 67
Warmus JS.da Silva MI. Org. Lett. 2000, 2: 1807 - 68
Zhang SQ.Fukase K.Kusumoto S. Tetrahedron Lett. 1999, 40: 7479 - 69
Lepore SD. Tetrahedron Lett. 2001, 42: 6437 - 70
Fleckenstein CA.Plenio H. Adv. Synth. Catal. 2006, 348: 1058 - 71
Leeb L.Gmeiner P.Lober S. QSAR Comb. Sci. 2007, 26: 1145 - 72
Li X.Abell C.Congreve MS.Warrington BH.Ladlow M. Org. Biomol. Chem. 2004, 2: 989 - 73
Lan P.Porco JA.South MS.Parlow JJ. J. Comb. Chem. 2003, 5: 660 - 74
Harned AM.Zhang MJ.Vedantham P.Mukherjee S.Herpel RH.Flynn DL.Hanson PR. Aldrichimica Acta 2005, 38: 3 - 75
Barrett AGM.Roberts RS.Schroder J. Org. Lett. 2000, 2: 2999 - 76
Moore JD.Harned AM.Henle J.Flynn DL.Hanson PR. Org. Lett. 2002, 4: 1847 - 77
Fuchter MJ.Hoffman BM.Barrett AGM. J. Org. Chem. 2005, 70: 5086 - 78
Dickerson TJ.Reed NN.Janda KD. Chem. Rev. 2002, 102: 3325 - 79
Ginisty M.Roy MN.Charette AB. J. Org. Chem. 2008, 73: 2542 -
80a
Stazi F.Marcoux D.Poupon JC.Latassa D.Charette AB. Angew. Chem. Int. Ed. 2007, 46: 5011 -
80b
Poupon JC.Boezio AA.Charette AB. Angew. Chem. Int. Ed. 2006, 45: 1415 -
80c
Poupon JC.Marcoux D.Cloarec JM.Charette AB. Org. Lett. 2007, 9: 3591 - 81
Perrier H.Labelle M. J. Org. Chem. 1999, 64: 2110 - 82
Bergbreiter DE.Liu Y.-S. Tetrahedron Lett. 1997, 38: 3703 -
83a
Bosanac T.Yang JM.Wilcox CS. Angew. Chem. Int. Ed. 2001, 40: 1875 -
83b
Bosanac T.Wilcox CS. Org. Lett. 2004, 6: 2321 -
83c
Bosanac T.Wilcox CS. J. Am. Chem. Soc. 2002, 124: 4194 -
84a
Bergbreiter DE.Blanton JR. J. Org. Chem. 1985, 50: 5828 -
84b
Bergbreiter DE. Chem. Rev. 2002, 102: 3345 - 85
Huang X.Witte KL.Bergbreiter DE.Wong C.-H. Adv. Synth. Catal. 2001, 343: 675 - 86
Haag R.Sunder A.Hebel A.Roller S. J. Comb. Chem. 2002, 4: 112 -
87a
Malenfant PRL.Jayaraman M.Frechet JMJ. Chem. Mater. 1999, 11: 3420 -
87b
Haag R. Chem. Eur. J. 2001, 7: 327 -
87c
van Heerbeek R.Kamer PCJ.van Leeuwen P.Reek JNH. Chem. Rev. 2002, 102: 3717 -
87d
Kim RM.Manna M.Hutchins SM.Griffin PR.Yates NA.Bernick AM.Chapman KT. Proc. Natl. Acad. Sci. U.S.A. 1996, 93: 10012 -
87e
Lu J.Toy PH. Chem. Rev. 2009, 109: 815 -
88a
Giguere RJ.Bray TL.Duncan SM.Majetich G. Tetrahedron Lett. 1986, 27: 4945 -
88b
Gedye R.Smith F.Westaway K.Ali H.Baldisera L.Laberge L.Rousell J. Tetrahedron Lett. 1986, 27: 279 - 89 inventors; NC 28106. CEM Corporation, PO Box 200,
3100 Smith Farm Rd, Matthews,
-
90a
Kappe CO. Angew. Chem. Int. Ed. 2004, 43: 6250 -
90b
Lidstrom P.Tierney J.Wathey B.Westman J. Tetrahedron 2001, 57: 9225 -
90c
Collins JM.Leadbeater NE. Org. Biomol. Chem. 2007, 5: 1141 -
90d
Strauss CR.Trainor RW. Aust. J. Chem. 1995, 48: 1665 - 91
Hayes BL, andCollins M. inventors; US Patent 6,744,024. - 92
Dabirmanesh Q.Roberts RMG. J. Organomet. Chem. 1993, 460: C28 - 93
Raner KD.Strauss CR.Trainor RW.Thorn JS.
J. Org. Chem. 1995, 60: 2456 -
94a
Ugi I.Steinbruckner C. Angew. Chem. 1960, 72: 267 -
94b
Ugi I. Angew. Chem. 1962, 74: 9 - 95
Chen JJ.Deshpande SV. Tetrahedron Lett. 2003, 44: 8873 - 96
Humphrey CE.Easson MAM.Tierney JP.Turner NJ. Org. Lett. 2003, 5: 849 -
97a
Lee CKY.Holmes AB.Ley SV.McConvey IF.Al-Duri B.Leeke GA.Santos RCD.Seville JPK. Chem. Commun. 2005, 2175 -
97b
Yu JQ.Wu HC.Ramarao C.Spencer JB.Ley SV. Chem. Commun. 2003, 678 -
97c
Ramarao C.Ley SV.Smith SC.Shirley IM.DeAlmeida N. Chem. Commun. 2002, 1132 - 98
Baxendale IR.Griffiths-Jones CM.Ley SV.Tranmer GK. Chem. Eur. J. 2006, 12: 4407 - 99
Arvela RK.Leadbeater NE. Org. Lett. 2005, 7: 2101 - 100
Singh BK.Appukkuttan P.Claerhout S.Parmar VS.Van der Eycken E. Org. Lett. 2006, 8: 1863 - 101
Katritzky AR.Zhang YM.Singh SK.Steel PJ. ARKIVOC 2003, (xv): 47 - 102
Mosse S.Alexakis A. Org. Lett. 2006, 8: 3577 -
103a
Rodriguez B.Bolm C. J. Org. Chem. 2006, 71: 2888 -
103b
Ibrahem I.Zou WB.Casas J.Sunden H.Cordova A. Tetrahedron 2006, 62: 357 -
103c
Ibrahem I.Casas J.Cordova A. Angew. Chem. Int. Ed. 2004, 43: 6528 - 104
Hosseini M.Stiasni N.Barbieri V.Kappe CO. J. Org. Chem. 2007, 72: 1417 -
105a
Suryanarayana C. Prog. Mater. Sci. 2001, 46: 1 -
105b
Volkov VV.Myakishev KG. Inorg. Chim. Acta 1999, 289: 51 - 106
Kaupp G. CrystEngComm 2009, 11: 388 -
107a
Wang G.-W.Komatsu K.Murata Y.Shiro M. Nature 1997, 387: 583 -
107b
Komatsu K.Wang G.-W.Murata Y.Tanaka T.Fujiwara K.Yamamoto K.Saunders M. J. Org. Chem. 1998, 63: 9358 -
108a
Rodríguez B.Bruckmann A.Rantanen T.Bolm C. Adv. Synth. Catal . 2007, 349: 2213 -
108b
Bruckmann A.Krebs A.Bolm C. Green Chem. 2008, 10: 1131 -
109a
Rodriguez B.Rantanen T.Bolm C. Angew. Chem. Int. Ed. 2006, 45: 6924 -
109b
Rantanen T.Schiffers I.Bolm C. Org. Process Res. Dev. 2007, 11: 592 - 110
Rodriguez B.Bruckmann A.Bolm C. Chem. Eur. J. 2007, 13: 4710 - 111
Kaupp G.Naimi-Jamal MR.Schmeyers J. Tetrahedron 2003, 59: 3753 - 112
Zhang Z.Gao J.Xia JJ.Wang GW. Org. Biomol. Chem. 2005, 3: 1617 - 113
Balema VP.Wiench JW.Pruski M.Pecharsky VK. J. Am. Chem. Soc. 2002, 124: 6244 -
114a
Tullberg E.Schacher F.Peters D.Frejd T. Synthesis 2006, 1183 -
114b
Tullberg E.Peters D.Frejd T.
J. Organomet. Chem. 2004, 689: 3778 - 115
Calo V.Nacci A.Monopoli A.Lopez L.di Cosmo A. Tetrahedron 2001, 57: 6071 -
116a
Fulmer DA.Shearouse WC.Medonza ST.Mack J. Green Chem. 2009, 11: 1821 -
116b
Thorwirth R.Stolle A.Ondruschka B. Green Chem. 2010, 12: 985 - 117
Naimi-Jamal MR.Mokhtari J.Dekamin MG.Kaupp G. Eur. J. Org. Chem. 2009, 3567 - 118
Prasad KRK.Joshi NN. J. Org. Chem. 1996, 61: 3888 -
119a
Tye H. Drug Discovery Today 2004, 9: 485 -
119b
Montgomery DC. Design and Analysis of Experiments 6th ed.: Wiley; New York: 2004. -
119c
Owen MR.Luscombe C.Lai LW.Godbert S.Crookes DL.Emiabata-Smith D. Org. Process Res. Dev. 2001, 5: 308 -
119d
Carlson R. Design and Optimisation in Organic Synthesis Elsevier; Amsterdam: 1992. -
119e
Rubin AE.Tummala S.Both DA.Wang CC.Delaney EJ. Chem. Rev. 2006, 106: 2794 -
119f
Carlson R.Carlson JE. Org. Process Res. Dev. 2005, 9: 680 -
119g
Stansbury WF. Chemometr.. Intell. Lab. Syst. 1997, 36: 199 -
119h
Gooding OW. Curr. Opin. Chem. Biol. 2004, 8: 297 -
119i
Guervenou J.Giamarchi P.Coulouarn C.Guerda M.Le Lez C.Oboyet T. Chemometr. Intell. Lab. Syst. 2002, 63: 81 -
119j
Emiabata-Smith DF.Crookes DL.Owen MR. Org. Process Res. Dev. 1999, 3: 281 - 120
Hogan PJ.Hopes PA.Moss WO.Robinson GE.Patel I. Org. Process Res. Dev. 2002, 6: 225 - 121
Navarrete-Bolanos JL.Jimenez-Islas H.Botello-Alvarez E.Rico-Martinez R. Org. Process Res. Dev. 2002, 6: 841 - 122
Jamieson C.Congreve MS.Emiabata-Smith DF.Ley SV. Synlett 2000, 1603 - 123
Gooding OW.Vo L.Battacharyya S.Labadie JW.
J. Comb. Chem. 2002, 4: 578 - 125
Jamieson C.Congreve MS.Emiabata-Smith DF.Ley SV.Scicinski JJ. Org. Process Res. Dev. 2002, 6: 823 - 127
Evans MD.Ring J.Schoen A.Bell A.Edwards P.Berthelot D.Nicewonger R.Baldino CM. Tetrahedron Lett. 2003, 44: 9337 - 128
Glasnov TN.Tye H.Kappe CO. Tetrahedron 2008, 64: 2035
References
Ace Glass Inc., P.O. Box 688, 1430 North West Blvd., Vineland, NJ 08362-0688, USA (product no. 5879)
124Anachem Instruments Ltd., Anachem House, Charles Street, Luton, Bedfordshire LU2 0EB, UK.
126Stat-Ease Inc., 2021 E. Hennepin Avenue, Suite 480, Minneapolis, MN 55413-2726, USA.
129Umetrics AB, Box 7960, 907 19 Umeå, Sweden.