Abstract
A series of PyBox ligands were prepared from commercially available
chelidonic acid by a multistep flow sequence using mesoreactor technology.
A chloro group introduced onto the ligand scaffold was subsequently
exploited to give amine derivatives ready for immobilization through
microencapsulation technologies.
Key words
ligands - macrocycles - flow chemistry - solid-supported reagent - asymmetric synthesis - scale up
References
1 Desimoni G.
Faita G.
Quadrelli P.
Chem.
Rev.
2003,
103:
3119
2a Evans DA.
Sweeny ZK.
Rovis T.
Tedrow JS.
J. Am. Chem. Soc.
2001,
123:
12095
2b Zhao C.-X.
Duffey MO.
Taylor SJ.
Morken JP.
Org.
Lett.
2001,
3:
1829
2c Keith JM.
Jacobsen EN.
Org.
Lett.
2004,
6:
153
2d Schaus SE.
Jacobsen EN.
Org.
Lett.
2000,
2:
1001
3a Bhattacharyya S.
Curr. Opin. Drug Discovery
Dev.
2004,
7:
752
3b Ley SV.
Baxendale IR.
Chem.
Rec.
2002,
2:
377
3c Ley SV.
Baxendale IR.
Nat.
Rev. Drug Discovery
2002,
1:
573
3d Kirschning A.
Monenschein H.
Wittenberg R.
Angew.
Chem. Int. Ed.
2001,
40:
650
3e Thompson LA.
Curr. Opin. Chem. Biol.
2000,
4:
324
4a Cornejo A.
Fraile JM.
García JI.
Gil MJ.
Luis SV.
Martínez-Merino V.
Mayoral JA.
J.
Org. Chem.
2005,
70:
5536
4b Cornejo A.
Fraile JM.
García JI.
García-Verdugo E.
Gil MJ.
Legarreta G.
Luis SV.
Martínez-Merino V.
Mayoral JA.
Org.
Lett.
2002,
4:
3927
5 Tilliet M.
Lundgren S.
Moberg C.
Levacher V.
Adv. Synth. Catal.
2007,
349:
2079
6 Zeng T.
Yang L.
Hudson R.
Song G.
Moores AR.
Li C.-J.
Org. Lett.
2011,
13:
442
7a Bremeyer N.
Ley SV.
Ramarao C.
Shirley IM.
Smith SC.
Synlett
2002,
1843
7b Yu J.-Q.
Wu HC.
Ramarao C.
Spencer JB.
Ley SV.
Chem.
Commun.
2003,
678
7c Mitchell C.
Pears D.
Ley SV.
Yu J.-Q.
Zhou W.
Org.
Lett.
2003,
5:
4665
7d Siu J.
Baxendale IR.
Ley SV.
Org. Biomol. Chem.
2004,
2:
160
7e Baxendale IR.
Griffiths-Jones CM.
Ley SV.
Tranmer GK.
Chem.
Eur. J.
2006,
12:
4407
7f Sedelmeier J.
Ley SV.
Lange H.
Baxendale IR.
Eur. J. Org. Chem.
2009,
4412
8a Kobayashi S.
Chem. Rev.
2009,
109:
594
8b Pears DA.
Smith SC.
Aldrichimica
Acta
2005,
38:
23
9a Nishijama H.
Sakaguchi H.
Nakamura T.
Horikata M.
Kondo M.
Kenji I.
Organometallics
1989,
8:
846
9b Desimoni G.
Faita G.
Guala M.
Pratelli C.
Tetrahedron: Asymmetry
2002,
13:
1651
9c Lundgren S.
Lutsenko S.
Jönsson C.
Moberg C.
Org. Lett.
2003,
5:
3663
10a Martin LJ.
Marzinzik AL.
Ley SV.
Baxendale IR.
Org. Lett.
2011,
13:
320
10b Baumann M.
Baxendale IR.
Kirschning A.
Ley SV.
Wegner J.
Heterocycles
2011,
82:
1297
10c Polyzos A.
Baxendale IR.
Petersen T.
Ley SV.
Angew. Chem. Int. Ed.
2011,
50:
1190
10d O’Brien M.
Baxendale IR.
Ley SV.
Org. Lett.
2010,
12:
1596
10e Hopkin MD.
Baxendale IR.
Ley SV.
Chem. Commun.
2010,
46:
2450
10f Qian Z.
Baxendale IR.
Ley SV.
Synlett
2010,
505
10g Carter CF.
Lange H.
Ley IR.
Baxendale IR.
Wittkamp B.
Goode JG.
Gaunt NL.
Org. Process Res. Dev.
2010,
14:
393
10h Malet-Sanz L.
Madrzak J.
Ley SV.
Baxendale IR.
Org. Biomol. Chem.
2010,
8:
5324
11a Riva E.
Rencurosi A.
G agliardi S.
Passarella D.
Martinelli M.
Chem. Eur. J.
2011,
17:
6221
11b Lange PP.
Gooßen LJ.
Podmore P.
Underwood T.
Sciammetta N.
Chem. Commun.
2011,
47:
3628
11c Batoul A.-O.
Sanderson AJ.
Org. Biomol. Chem.
2011,
9:
3854
11d Rasheed M.
Elmore SC.
Wirth T. In
Catalytic Methods in Asymmetric Synthesis:
Advanced Materials, Techniques, and Applications
Gruttadauria M.
Giacalone F.
Wiley;
Hoboken:
2011.
p.345
11e Ahmed-Omer B.
Barrow DA.
Wirth T.
ARKIVOC
2011,
(iv):
26
11f Rasheed M.
Wirth T.
Angew. Chem. Int. Ed.
2011,
50:
357
11g Brandt JC.
Elmore SC.
Robinson RI.
Wirth T.
Synlett
2010,
3099
11h Brasholz M.
Macdonald JM.
Saubern S.
Ryan JH.
Holmes AB.
Chem.
Eur. J.
2010,
16:
11471
11i Wegner J.
Ceylan S.
Friese C.
Kirschning A.
Eur. J. Org. Chem.
2010,
4372
11j Grafton M.
Mansfield AC.
Fray MJ.
Tetrahedron Lett.
2010,
51:
1026
11k Tamborini L.
Conti P.
Pinto A.
Micheli CD.
Tetrahedron: Asymmetry
2010,
21:
222
11l Bogdan AR.
Poe SL.
Kubis DC.
Broadwater SJ.
McQuade DT.
Angew. Chem. Int.
Ed.
2009,
48:
8547
11m Seeberger PH.
Nat. Chem.
2009,
1:
258
11n Bogdan A.
McQuade DT.
Beilstein J. Org.
Chem.
,
11o Rolland J.
Cambeiro XC.
Rodríguez-Escrich C.
Pericàs MA.
Beilstein
J. Org. Chem.
2009,
5:
56
11p Hessel V.
Chem.
Eng. Technol.
2009,
32:
1655
12 The use of a standard T or Y union
gave rise to problems of back-mixing and build-up of blockages in
the flow channel.
13 Browne DL.
Deadman BJ.
Ashe R.
Baxendale IR.
Ley SV.
Org. Process Res. Dev.
2011,
15:
693
14 Sedelmeier J.
Ley SV.
Baxendale IR.
Baumann M.
Org. Lett.
2010,
12:
3618
15a Tse M. K.
Bhor S.
Klawonn M.
Anikumar G.
Jiao H.
Döbler C.
Spannenberg A.
Mägerlein W.
Hugl H.
Beller M.
Chem. Eur.
J.
2006,
12:
1855
15b Bhattacharya S.
Snehalatha K.
Kumar V. P.
J. Org. Chem.
2003,
68:
2741
16 Clayden J.
Organic
chemistry
Oxford University Press;
Oxford:
2001.
p.276-296
17 Commercially available from TCI Europe:
Vilsmeier reagent N -(chloromethylene)-N -methylmethanaminium chloride [CAS
Reg. No. 3724-43-4].
18 The Vapourtec R2+/R4
flow system used in this study is commercially available from Vapourtec;
Web site: http://www.vapourtec.co.uk.
19 Quadrapure-DMA. Available from Johnson
Matthey, see: http://www.scavengingtechnologies.com/site.asp?id = 1297&pageid = 1299.
20a Parsons AT.
Johnson JS.
J. Am. Chem. Soc.
2009,
131:
3122
20b Wang H.
Wang H.
Liu P.
Yang H.
Xiao J.
Can Li C.
J. Mol. Catal. A: Chem.
2008,
285:
128
21a Mammoliti O.
Allasia S.
Dixon S.
Kilburn JD.
Tetrahedron
2009,
65:
2184
21b Bradshaw JS.
Colter ML.
Nakatsuji Y.
Spencer NO.
Brown MF.
Izatt RM.
Arena G.
Tse P.-K.
Wilson BE.
Lamb JD.
Dalley NK.
J. Org. Chem.
1985,
50:
4865
22 Baumann M.
Baxendale IR.
Ley SV.
Synlett
2008,
2111
23 Baumann M.
Baxendale IR.
Martin LJ.
Ley SV.
Tetrahedron
2009,
65:
6611
24a Smith CJ.
Smith CD.
Nikbin N.
Ley SV.
Baxendale IR.
Org. Biomol. Chem.
2011,
9:
1927
24b Smith CJ.
Nikbin N.
Ley SV.
Lange H.
Baxendale IR.
Org. Biomol. Chem.
2011,
9:
1938
24c Smith CD.
Baxendale IR.
Lanners S.
Hayward JJ.
Smith SC.
Ley SV.
Org.
Biomol. Chem.
2007,
5:
1559
24d Baumann M.
Baxendale IR.
Ley SV.
Nikbin N.
Smith CD.
Org. Biomol. Chem.
2008,
6:
1587
24e Baumann M.
Baxendale IR.
Ley SV.
Nikbin N.
Smith CD.
Tierney JP.
Org.
Biomol. Chem.
2008,
6:
1577
24f Baxendale IR.
Deeley J.
Griffiths-Jones CM.
Ley SV.
Saaby S.
Tranmer GK.
Chem.
Commun.
2006,
2566
25 Bryan MC.
Wernick D.
Hein CD.
Petersen JV.
Eschelbach JW.
Doherty EM.
Beilstein J. Org.
Chem.
2011,
7:
1141
26 Horvath G.
Rusa C.
Montos Z.
Gerencser J.
Huszthy P.
Synth. Commun.
1999,
29:
3719
27 Preston AJ.
Gallucci JC.
Parquette JR.
Chem. Commun.
2005,
3280
28 Bradshaw JS.
Huszthy P.
Wang T.-M.
Zhu C.-Y.
Nazarenko AZ.
Izatt RM.
Supramol. Chem.
1993,
1:
267
29 Chessa G.
Canovese L.
Visentin F.
Santo C.
Seraglia R.
Tetrahedron
2005,
61:
1755
