Preparation of ferrocenyl imidazolines using bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate

Science in China, Series B: Chemistry

Volumn 52, Issue 9, 2009, Pages 1331-1336

  Wang, Xueqiang ^a   Xia, Jibao ^a   Dai, Xiaoyang ^a   You, Shuli ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Asymmetric catalysis; Chiral; Dehydration; Ferrocene; Imidazoline

Indexed keywords

ASYMMETRIC CATALYSIS; CHIRAL; EFFICIENT SYNTHESIS; FERROCENE; FERROCENYL; FERROCENYL CARBOXYLIC AMIDE; IMIDAZOLINE; IMIDAZOLINES; SIDE CHAINS;

AMIDES; AMINES; CARBOXYLIC ACIDS; CATALYSIS; DEHYDRATION; DEWATERING; IRON COMPOUNDS;

ORGANIC ACIDS;

EID: 70349522424     PISSN: 10069291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-009-0161-5     Document Type: Article

References (35)

1. Hayashi T, Togni A. Eds. In Ferrocenes. VCH: Weinheim, Germany, 1995
2. Togni A, Haltermann R L. eds. In Metallocenes. VCH: Weinheim, Germany, 1998
3. C. F. Richards A. J. Locke 1998 Recent advances in the generation of non-racemic ferrocene derivatives and their application to asymmetric synthesis Tetrahedron: Asymmetry 9 2377 2407 10.1016/S0957-4166(98)00251-1 1:CAS:528:DyaK1cXlsFOnu7g%3D (Pubitemid 28374934)
4. L. X. Dai T. Tu S. L. You W.-P. Deng X. L. Hou 2003 Asymmetric catalysis with chiral ferrocene ligands Acc Chem Res 36 659 667 10.1021/ar020153m 1:CAS:528:DC%2BD3sXktVKrtbs%3D
5. R. C. J. Atkinson V. C. Gibson N. J. Long 2004 The syntheses and catalytic applications of unsymmetrical ferrocene ligands Chem Soc Rev 33 313 328 10.1039/b316819k 1:CAS:528:DC%2BD2cXks1Chs7w%3D (Pubitemid 38960704)
6. R. G. Arrayás J. Adrio J. C. Carretero 2006 Recent applications of chiral ferrocene ligands in asymmetric catalysis Angew Chem Int Ed 45 7674 7715 10.1002/anie.200602482 (Pubitemid 44871323)
7. You S L, Zhou Y-G, Hou X L, Dai L X. Enantioselective palladium catalyzed allylic substitution with chiral thioether derivatives of ferrocenyl-oxazoline and the role of planar chirality in this reaction. Chem Commun, 1998, 2765-2766
8. S. L. You X. L. Hou L. X. Dai 2000 Synthesis of planar chiral selenide derivatives of ferrocenyl-oxazoline and their application in enantioselective palladium catalyzed allylic substitution reaction Tetrahedron: Asymmetry 11 1495 1500 10.1016/S0957-4166(00)00078-1 1:CAS:528:DC%2BD3cXjsFylt70%3D (Pubitemid 30316381)
9. W. P. Deng S. L. You X. L. Hou L. X. Dai Y. H. Yu W. Xia J. Sun 2001 Importance of planar chirality in chiral catalysts with three chiral elements: The role of planar chirality in 2'-substituted 1,1'-P,N- ferrocene ligands on the enantioselectivity in Pd-catalyzed allylic substitution J Am Chem Soc 123 6508 6519 10.1021/ja002657q 1:CAS:528:DC%2BD3MXktlalt7Y%3D (Pubitemid 32923022)
10. S. L. You X. Z. Zhu Y. M. Luo X. L. Hou L. X. Dai 2001 Highly regio- and enantioselective Pd-catalyzed allylic alkylation and amination of monosubstituted allylic acetates with novel ferrocene P,N-ligands J Am Chem Soc 123 7471 7472 10.1021/ja016121w 1:CAS:528:DC%2BD3MXkvFKqs7s%3D (Pubitemid 32879483)
11. S. L. You X. L. Hou L. X. Dai Y. H. Yu W. Xia 2002 Role of planar chirality of S,N- and P,N-ferrocene ligands in Palladium-catalyzed allylic substitutions J Org Chem 67 4684 4695 10.1021/jo016330z 1:CAS:528: DC%2BD38Xjslensb8%3D (Pubitemid 34742697)
12. J. Ma X. Cui L. Gao Y. Wu 2007 Ferrocenylimidazoline palladacycles: Syntheses, crystal structures and applications as catalysts for Suzuki cross coupling reaction in water Inorg Chem Commun 10 762 766 10.1016/j.inoche.2007. 03.018 1:CAS:528:DC%2BD2sXmt1yls78%3D
13. J. Ma X. L. Cui B. Zhang M. P. Song Y. J. Wu 2007 Ferrocenylimidazoline palladacycles: efficient phosphine-free catalysts for Suzuki-Miyaura cross-coupling reaction Tetrahedron 63 5529 5538 10.1016/j.tet.2007.04.022 1:CAS:528:DC%2BD2sXlsFKhsL0%3D (Pubitemid 46778866)
14. R. Peters D. F. Fischer 2005 Preparation and diastereoselective ortho-metalation of chiral ferrocenyl imidazolines: Remarkable influence of LDA as metalation additive Org Lett 7 4137 4140 10.1021/ol051437k 1:CAS:528:DC%2BD2MXpt1Whsbo%3D (Pubitemid 41361548)
15. R. Peters Z. Q. Xin D. F. Fischer W. B. Schweizer 2006 Synthesis and diastereoselective ortho-lithiation/cyclopalladation of enantiopure [2-imidazolyl]-1',2',3',4',5'-pentamethylferrocenes and -1',2',3',4', 5'-pentaphenylferrocenes Organometallics 25 2917 2920 10.1021/om060187o 1:CAS:528:DC%2BD28XjvFKqs74%3D (Pubitemid 44020711)
16. M. E. Weiss D. F. Fischer Z. Q. Xin S. Jautze W. B. Schweizer R. Peters 2006 Practical, highly active, and enantioselective ferrocenyl-imidazoline palladacycle catalysts (FIPs) for the aza-Claisen rearrangement of N-para-methoxyphenyl trifluoroacetimidates Angew Chem Int Ed 45 5694 5698 10.1002/anie.200601731 1:CAS:528:DC%2BD28XpsVCgtLw%3D (Pubitemid 44366779)
17. S. Jautze P. Seiler R. Peters 2007 Macrocyclic ferrocenyl-bisimidazoline palladacycle dimers as highly active and enantioselective catalysts for the aza-Claisen rearrangement of Z-configured N-para-methoxyphenyl trifluoroacetimidates Angew Chem Int Ed 46 1260 1264 10.1002/anie.200603568 1:CAS:528:DC%2BD2sXit1Sju70%3D (Pubitemid 46991787)
18. D. F. Fischer Z. Q. Xin R. Peters 2007 Asymmetric formation of allylic amines with N-substituted quaternary stereocenters by PdII-catalyzed aza-Claisen rearrangements Angew Chem Int Ed 46 7704 7707 10.1002/anie.200702086 1:CAS:528:DC%2BD2sXht1SisLjN (Pubitemid 47557031)
19. S. Jautze P. Seiler R. Peters 2008 Synthesis of nearly enantiopure allylic amines by aza-Claisen rearrangement of Z-configured alylic trifluoroacetimidates catalyzed by highly active ferrocenylbispalladacycles Chem Eur J 14 1430 1444 10.1002/chem.200701642 1:CAS:528:DC%2BD1cXkvFalur8%3D
20. Xin Z-q, Fischer D F, Peters R. Catalytic asymmetric formation of secondary allylic amines by aza-Claisen rearrangement of trifluoroacetimidates. Synlett, 2008, 1495-1499
21. S. Jautze R. Peters 2008 Enantioselective bimetallic catalysis of michael additions forming quaternary stereocenters Angew Chem Int Ed 47 9284 9288 10.1002/anie.200803539 1:CAS:528:DC%2BD1cXhsVygtLjE
22. T. K. Hollis L. E. Overman 1999 Palladium catalyzed enantioselective rearrangement of allylic imidates to allylic amides J Organomet Chem 576 290 299 10.1016/S0022-328X(98)01065-1 1:CAS:528:DyaK1MXivFOls70%3D
23. C. E. Anderson L. E. Overman 2003 Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity J Am Chem Soc 125 12412 12413 10.1021/ja037086r 1:CAS:528:DC%2BD3sXntlyku78%3D (Pubitemid 37254751)
24. L. E. Overman C. E. Owen M. M. Pavan C. J. Richards 2003 Catalytic asymmetric rearrangement of allylic N-aryl trifluoroacetimidates. A useful method for transforming prochiral allylic alcohols to chiral allylic amines Org Lett 5 1809 1812 10.1021/ol0271786 1:CAS:528:DC%2BD3sXjsVOgsbs%3D (Pubitemid 37161930)
25. S. F. Kirsch L. E. Overman M. P. Watson 2004 Monomeric cobalt oxazoline palladacycles (COP). Useful catalysts for catalytic asymmetric rearrangement of allylic trichloroacetimidates J Org Chem 69 8101 8104 10.1021/jo0487092 1:CAS:528:DC%2BD2cXotlSisrc%3D (Pubitemid 39507422)
26. R. S. Prasad C. E. Anderson C. J. Richards L. E. Overman 2005 Synthesis of tert-leucine-derived cobalt oxazoline palladacycles. Reversal of palladation diastereoselectivity and application to the asymmetric rearrangement of N-aryl trifluoroacetimidates Organometallics 24 77 81 10.1021/om0493614 1:CAS:528:DC%2BD2cXhtVans7jO (Pubitemid 40121564)
27. C. E. Anderson Y. Donde C. J. Douglas L. E. Overman 2005 Catalytic asymmetric synthesis of chiral allylic amines. Evaluation of ferrocenyloxazoline palladacycle catalysts and imidate motifs J Org Chem 70 648 657 10.1021/jo048490r 1:CAS:528:DC%2BD2cXhtFCiu7nF (Pubitemid 40129429)
28. H. Nomura C. J. Richards 2007 An investigation into the allylic imidate rearrangement of trichloroacetimidates catalysed by cobalt oxazoline palladacycles Chem Eur J 13 10216 10224 10.1002/chem.200700873 1:CAS:528:DC%2BD1cXltFSitbk%3D
29. S.-L. You H. Razavi J. W. Kelly 2003 A biomimetic synthesis of thiazolines using hexaphenyloxodiphosphonium trifluoromethanesulfonate Angew Chem Int Ed 42 83 3363 10.1002/anie.200390059 1:CAS:528:DC%2BD3sXmvFyjsQ%3D%3D (Pubitemid 36109504)
30. S. L. You J. W. Kelly 2003 Total synthesis of Dendroamide A: Oxazole and thiazole construction using an oxodiphosphonium salt J Org Chem 68 9506 9509 10.1021/jo0302657 1:CAS:528:DC%2BD3sXovVClsr8%3D (Pubitemid 37456529)
31. S. L. You J. W. Kelly 2004 Highly efficient biomimetic total synthesis and structural verification of bistratamides E and J from Lissoclinum bistratum Chem Eur J 10 71 75 10.1002/chem.200305504 1:CAS:528:DC%2BD2cXlvVGitg%3D%3D
32. S. L. You D. Songpon J. W. Kelly 2004 Solid-phase synthesis and stereochemical assignments of tenuecyclamides A-D employing heterocyclic amino acids derived from commercially available Fmoc α-amino acids Org Lett 6 2627 2730 10.1021/ol049020m 1:CAS:528:DC%2BD2cXltVKrt78%3D (Pubitemid 39077785)
33. S. L. You J. W. Kelly 2005 The total synthesis of bistratamides F-I Tetrahedron 61 241 249 10.1016/j.tet.2004.10.024 1:CAS:528:DC%2BD2cXhtVCqs77O (Pubitemid 39573422)
34. S. L. You J. W. Kelly 2005 Total synthesis of didmolamides A and B Tetrahedron Lett 46 2567 2570 10.1016/j.tetlet.2005.02.097 1:CAS:528: DC%2BD2MXisVCgtLo%3D (Pubitemid 40386414)
35. S. L. You J. W. Kelly 2004 Highly efficient enantiospecific synthesis of imidazoline-containing amino acids using bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate Org Lett 6 1681 1683 10.1021/ol049439c 1:CAS:528:DC%2BD2cXjt1Ggs78%3D (Pubitemid 38698480)