Abstract
A series of novel C
2 -symmetric bis(thiazoline) ligands with dibenzo[a ,c ]cycloheptadiene backbone as the substituent on the thiazoline ring were synthesized using the simple reagent phosphorus pentasulfide, and their application in catalytic allylic alkylation was investigated by comparison with the corresponding bis(oxazolines). Palladium-bis(oxazoline) complexes furnished good enantioselectivity (up to 87% ee), while bis(thiazolines) only gave up to moderate enantioselectivity (56% ee) with CH2 Cl2 as solvent. Preliminary explanation of the catalysis mechanism is given for the difference of two types of Pd(0)-ligand complexes.
Key words
bis(thiazolines) - bis(oxazolines) - synthesis - allylic alkylation - asymmetric catalysis
References
1a Johannsen M.
Jorgensen KA.
Chem. Rev.
1998,
98:
1689
1b Trost BM.
van Vranken DL.
Chem. Rev.
1996,
96:
395
1c Comprehensive Asymmetric Catalysis
Vol. 2:
Jacobsen EN.
Pfaltz A.
Yamamoto H.
Springer-Verlag;
Berlin:
1999.
Chap. 24.
1d Reiser O.
Angew. Chem., Int. Ed. Engl.
1993,
32:
547
1e Frost CG.
Howarth J.
Williams JMJ.
Tetrahedron: Asymmetry
1992,
3:
1089
2a Dawson GJ.
Frost CG.
Williams JMJ.
Tetrahedron Lett.
1993,
34:
3149
2b von Matt P.
Pfaltz A.
Angew. Chem., Int. Ed. Engl.
1993,
32:
566
2c von Matt P.
Loiseleur O.
Koch G.
Pfaltz A.
Tetrahedron
1994,
5:
573
2d von Matt P.
Lloyd-Jones GC.
Minidis ABE.
Pfaltz A.
Macko L.
Neuburger M.
Zehnder M.
Rüegger H.
Pregosin PS.
Helv. Chim. Acta
1995,
78:
265
2e Sprinz J.
Helmchen G.
Tetrahedron Lett.
1993,
34:
1769
2f Sprinz J.
Kiefer M.
Helmchen G.
Reggelin M.
Huttner G.
Walter O.
Zsolnai L.
Tetrahedron Lett.
1994,
35:
1523
3a Gilbertson SR.
Chang CWT.
J. Org. Chem.
1998,
63:
8424
3b Gilbertson SR.
Xie D.
Angew. Chem., Int. Ed.
1999,
38:
2750
3c Nishibayashi Y.
Takei I.
Uemura S.
Hidai M.
Organometallics
1998,
17:
3420
3d Zhang WB.
Yoneda Y.
Kida T.
Nakatsuji Y.
Ikeda I.
Tetrahedron: Asymmetry
1998,
9:
3371
3e Jiang Y.
Jiang Q.
Zhu G.
Zhang X.
Tetrahedron Lett.
1997,
38:
215
3f Togni A.
Venanzi LM.
Angew. Chem., Int. Ed.
1994,
33:
497
4a Voituriez A.
Schulz E.
Tetrahedron: Asymmetry
2003,
14:
339
4b Wu H.
Wu XW.
Hou XL.
Dai LX.
Wang QR.
Chin. J. Chem.
2002,
20:
816 ; Chem. Abstr.
2003 , 138 , 187675
5a Bayardon J.
Sinou D.
Tetrahedron Lett.
2003,
44:
1449
5b Patti A.
Lotz M.
Knochel P.
Tetrahedron: Asymmetry
2002,
12:
3375
5c Kaiser NFK.
Bremberg U.
Larhed M.
Moberg C.
Hallberg A.
J. Organomet. Chem.
2000,
603:
2
5d Gómez M.
Jansat S.
Muller G.
Maestro MA.
Mahía J.
Organometallics
2002,
21:
1077
6a Ghosh AK.
Mathivanan P.
Cappiello J.
Tetrahedron: Asymmetry
1998,
9:
1
6b Johnson JS.
Evans DA.
Acc. Chem. Res.
2000,
33:
325
6c Braunstein P.
Naud F.
Angew. Chem., Int. Ed.
2001,
40:
680
7a Andrus MB.
Zhou ZN.
J. Am. Chem. Soc.
2002,
124:
8806
7b Zhuang W.
Gathergood N.
Hazell RG.
Jorgensen KA.
J. Org. Chem.
2001,
66:
1009
7c Denmark SE.
Stiff CM.
J. Org. Chem.
2000,
65:
5875
7d Yao S.
Roberson M.
Reichel F.
Hazell RG.
Jorgensen KA.
J. Org. Chem.
1999,
64:
6677
7e Jensen KB.
Hazell RG.
Jorgensen KA.
J. Org. Chem.
1999,
64:
2353
8a Tárraga A.
Molina P.
Curiel D.
Bautista D.
Tetrahedron: Asymmetry
2002,
13:
1621
8b Abrunhosa I.
Gulea M.
Levillain J.
Masson S.
Tetrahedron: Asymmetry
2001,
12:
2851
8c Lafargue P.
Guenot P.
Lellouche JP.
Synlett
1995,
171
9a Du DM.
Wang ZY.
Xu DC.
Hua WT.
Synthesis
2002,
2347
9b Wang ZY.
Du DM.
Wu D.
Hua WT.
Synth. Commun.
2003,
33:
1275
9c Xu DC.
Du DM.
Ji N.
Wang ZY.
Hua WT.
Synth. Commun.
2003,
33:
2563
10a Du DM.
Fu B.
Hua WT.
Tetrahedron
2003,
59:
1933
10b Fu B.
Du DM.
Chin. J. Chem.
2003,
21:
597 ; Chem. Abstr. 2003 , 139 , 197411
10c Fu B.
Du DM.
Wang JB.
Tetrahedron: Asymmetry
2004,
15:
119
11a Nishio T.
Sekiguchi H.
Heterocycles
2002,
58:
203
11b Aimar ML.
Kreiker J.
de Rossi RH.
Tetrahedron Lett.
2002,
43:
1947
11c Peyrane F.
Fourrey JL.
Clivio P.
Chem. Commun.
2003,
736
12 Zhang YX.
Chen ZY.
Zhang HB.
Chen SF.
Chin. J. Synth. Chem.
2002,
10:
266 ; Chem. Abstr. 2003 , 138 , 187707
13a Hashizume T.
Yonehara K.
Ohe K.
Uemura S.
J. Org. Chem.
2000,
65:
5197
13b Wimmer P.
Widhalm M.
Tetrahedron: Asymmetry
1995,
6:
657
14a Müller D.
Umbricht G.
Weber B.
Pfaltz A.
Helv. Chim. Acta
1991,
74:
232
14b Chelucci G.
Deriu S.
Pinna GA.
Saba A.
Valenti R.
Tetrahedron : Asymmetry
1999,
10:
3803
15 Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC-216676. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].
16 Sheldrick GM.
SHELXS 98, Program for the Solution of Crystal Structures
University of Göttingen;
Germany:
1998.
17 Sheldrick GM.
SHELXL 98, Program for the Refinement of Crystal Structures
University of Göttingen;
Germany:
1998.
