plus lucis fortbildungswoche feb 25. 2015 catalytic ... · catalytic rearrangements as tools in...
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Catalyticrearrangements
astoolsinorganicsynthesis
Nuno MaulideUniversity of Vienna
Institute of Organic Chemistry
Plus Lucis FortbildungswocheFeb 25. 2015
From design to serendipitous discovery... And back
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2
Overviewof researchintheMaulideGroup(2009‐2015)
Amide activation methodologies
Cyclobutene synthesis and chemistry
Nu
CO2H
H
HO O
"f lat" achiralstarting mater ial
2) Nucleophile Nu
1) h
f unctionalisedcyclobutene
Angew. Chem. 2010, 122, 5807Angew. Chem. 2011, 123, 12840
Synlett 2011, 22, 735Angew. Chem. 2012, 124, 2869Angew. Chem. 2012, 124, 7426ChemCatChem 2013, 5, 1239
Synlett 2013, 24, 1286Chem. Eur. J. 2013, 19, 6566
Angew. Chem. 2013, 125, 6434Org. Lett. 2013, 15, 2318
Angew. Chem. 2013, 125, 9845Angew. Chem. 2014, 126, 7188
Organic redox‐neutral reactions
New perspectives on the chemistry of Sulfur
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3
Overviewof researchintheMaulideGroup(2009‐2015)
Amide activation methodologies
Cyclobutene synthesis and chemistry
Nu
CO2H
H
HO O
"f lat" achiralstarting mater ial
2) Nucleophile Nu
1) h
f unctionalisedcyclobutene
Angew. Chem. 2010, 122, 5807Angew. Chem. 2011, 123, 12840
Synlett 2011, 22, 735Angew. Chem. 2012, 124, 2869Angew. Chem. 2012, 124, 7426ChemCatChem 2013, 5, 1239
Synlett 2013, 24, 1286Chem. Eur. J. 2013, 19, 6566
Angew. Chem. 2013, 125, 6434Org. Lett. 2013, 15, 2318
Angew. Chem. 2013, 125, 9845Angew. Chem. 2014, 126, 7188
Organic redox‐neutral reactions
New perspectives on the chemistry of Sulfur
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Fomannosin:retrosynthesisvia [2+2]cycloadditionchemistry
Ghosez, L.; Marchand‐Brynaert, J., Adv. Org. Chem. 1976, 9, Pt. 1, 421
Snider, B. B., Chem. Rev. 1988, 88, 793
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Chemistryofketeniminiumsalts
Keteniminium salts are a class of heterocumulenes that are characterized by the cumulative arrangement of olefin and iminium groups.
L. Ghosez, J. Marchand‐Brynaert, in Iminium Salts in Organic Chemistry, Part 1 (Eds.: H. Böhme, H. G. Viehe), Wiley: New York, New York, 1976, pp. 421.J. C. Jochims et al., Chem. Ber. 1982, 115, 172.C. Madelaine, V. Valerio, N. Maulide, Chem. Asian J. 2011, 6, 2224.
Characteristic: high reactivity toward nucleophilic reagents
Generally unstable.Stable long‐lived keteniminium salts are only possible under special conditions and
require weakly nucleophilic counterions (BF4‐, ZnCl3‐, PF6‐)
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Preparationofketeniminiumsalts
‐ by protonation of ynamines or ynamides
‐ from ‐(pseudo)haloenamines
‐ by alkylation of the corresponding ketenimines at nitrogen
F. Hallmann, Ber. Dtsch. Chem. Ges., 1876, 9, 846; L. Ghosez et al., Adv. Org. Chem. 1976, 9, Pt.1, 421.Deyrup, J. A. and Kuta, G. S. J. Org. Chem. 1978, 43, 501.J. Ficini, C. Barbara, Tetrahedron Lett. 1966, 6425; DeKorver, K. A., Li, H., Lohse, A. G., Hayashi, R., Lu, Z., Zhang, Y., Hsung, R. P. Chem. Rev. 2010, 110, 5064
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TypicalreactivityofKeteniminiumSalts:2+2cycloaddition
J. Marchand‐Brynaert, L. Ghosez, J. Am. Chem. Soc. 1972, 94, 2870.B.B. Snider, Chem. Rev. 1988, 88, 793.C. Madelaine, V. Valerio, N. Maulide, Chem. Asian J. 2011, 6, 2224
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BacktotheRetrosyntheticplan
Ghosez, L.; Marchand‐Brynaert, J., Adv. Org. Chem. 1976, 9, Pt. 1, 421Snider, B. B., Chem. Rev. 1988, 88, 793
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Unexpectedobservation
Ghosez, L.; Marchand‐Brynaert, J., Adv. Org. Chem. 1976, 9, Pt. 1, 421Snider, B. B., Chem. Rev. 1988, 88, 793
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ElectrophilicAmideActivation
With Claire Madelaine and Viviana Valerio:Angew. Chem. 2010, 122, 1628Chem. Eur. J. 2011, 17, 4742Chem. Asian J. 2011, 6, 2224
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Carbonyl ‐Arylation
Reviews: (a) Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 1082. (b) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450. (c) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234
Arynes: Tadross, P. M.; Gilmore, C. D.; Bugga, P.; Virgil, S. C.; Stoltz, B. M. Org. Lett. 2010, 12, 1224 Organobismuth reagents: (a) Barton, D. H. R.; Finet, J.‐P. Pure Appl. Chem. 1987, 59, 937. (b) Elliott, G.; Konopelski, J. P. Tetrahedron 2001, 57, 5683. Organolead reagents: (a) Orito, K.; Sasaki, T.; Suginome, H. J. Org. Chem. 1995, 60, 6208. (b) Xia, J.; Brown, L. E.; Konopelski, J. P. J. Org. Chem. 2007, 72, 6885.
Hypervalent iodine: (a) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299. (b) Olofsson, B.; Merritt, E. A. Angew. Chem. Int. Ed. 2009, 48, 9052.
Xu, Q.-L.; Gao, H.; Yousufuddin, M.;Ess, D. H.; Kurti, L. J. Am. Chem. Soc. 2013, 135, 14048
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Initialreactiondesign
Chem. Eur. J. 2011, 17, 4742With Claire Madelaine and Viviana Valerio: Angew. Chem. Int. Ed. 2010, 49, 1583
35-90% yieldsLimited scope
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Unexpectedobservation
Xueliang Huang
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Ylidetransferreactions
With Xueliang Huang : Angew. Chem. Int. Ed. 2010, 49, 8979;Angew. Chem. 2010, 122, 9163.
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Ylidetransferrevisited
Xueliang Huang
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Towardsmetal‐freearylations
With Xueliang Huang: J. Am. Chem. Soc. 2011, 133, 8510
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Towardsmetal‐freearylations:enlargedscope
With Xueliang Huang, Mahendra Patil, Walter Thiel and Christophe Farès, J. Am. Chem. Soc. 2013, 135, 7312‐7323.
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Mechanisticconsiderations
With Xueliang Huang, Mahendra Patil, Walter Thiel and Christophe Farès, J. Am. Chem. Soc. 2013, 135, 7312‐7323Cf: Procter, Angew.Chem. Int. Ed. 2013, 52, 4008 Ujaque and Asensio, Org. Lett. 2009, 11, 4906
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Opportunitiesforfurtherchemistry?
With Bo Peng, Xueliang Huang and Langui Xie
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Theimportanceofasulfoxide
With Bo Peng, Xueliang Huang and Langui XieCf: R. P. Hsung, Chem. Rev. 2010, 110, 5064
Tetrahedron 2006, 62, 3928
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Keteniminiummeetssulfoxides
With Bo Peng, Xueliang Huang and Langui Xie, Angew. Chem. Int. Ed. 2014, 53, 8718(Selected as a Hot Paper by the Editorial Office)
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Keteniminiummeetssulfoxides– again
RO R
NO
N
SR1
electrophilic activation PhS
R1
O
SO
R1
NR
N
OTf2O, several pyridine bases N
O
PhSPh2SO
nada
With Bo Peng and Danny Geerdink
First part of this lecture!
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Keteniminiummeetssulfoxides– again
N
O
PhSN
O
PhS
N
O
PhSMeO
N
OPh
PhSN
O
PhS
N
O
PhS
N
O
PhS
ClN
O
PhS
90% 83%
84%
50% 76%
60%71% 75%
9 5
O
3 3
O
R1N
O
R3
R2R1
N
O
R3
R2
RS
O
PhS
MeO
O
78%
N
2-iodopyridine, Tf2O
0°C, 15 min. 0 °C to rt, 12 h
SR
O
O
NS
Me
O
NS
Me
Cl
O
NS
Bn
83% 64% 84%
With Bo Peng, Danny Geerdink and Christophe Farès, Angew. Chem. Int. Ed. 2014, 53, 5462(Selected as a VIP Article by the Editorial Office)
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AmideActivation
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Notonlysulfoxides– towardsageneralapproach? (Outlook)
Unpublished results (Bo Peng, Langui Xie, Daniel Kaiser, Mohan Padmanaban)
RO R
NO
N
SR1
electrophilic activation PhS
R1
O
SO
R1
NR
RO R
NO
N
XR1
electrophilic activation PhX
R1
O
XO
R1
NR
R1N
O
0 °C to rt, 24 h
NOH
Ph
O HNPh
O
N
O
HNPh
O
ClN
O
HNPh
O
3
64% 59%
R1N
O2-iodopyridine, Tf2O
0°C, 15 min.
N
O
HNPh
O
MeO
O
5
60%
Conversions to indoles and oxindoles: J. May, Org. Lett. 2013, 15, 1666T. Driver Org. Lett. 2014, 16, 2916
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C‐Hfunctionalisation
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C‐Hfunctionalisation
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Redox‐neutralC‐Hfunctionalisation
Internal redox‐neutral C‐H activation + cyclisation
D. N. Reinhoudt J. Org. Chem. 1988, 53, 2278. M. Noguchi J. Chem. Soc., Perkin Trans. 1, 1998, 3327.D. Sames J. Am. Chem. Soc. 2005, 127, 12180 and Org. Lett. 2005, 24, 5419.Also cf: O. Meth‐Cohn, Adv. Heterocycl. Chem. 1972, 14, 211
Asymmetric catalysis:D. Seidel et al. J. Am. Chem. Soc. 2009, 131, 13226 D. Y. Kim et al. J. Am. Chem. Soc. 2010, 132, 11847T. Akiyama et al. J. Am. Chem. Soc. 2011, 133, 6166
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AmineC‐Hfunctionalisation
Reviews on CDC coupling: C.‐J. Li, Acc. Chem. Res. 2009, 42, 335 C. J. Scheuermann, Chem. Asian J. 2010, 5, 436 M. Klussmann, D. Sureshkumar, Synthesis 2011, 3, 353
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AmineC‐Hfunctionalisation:partI
Igor Jurberg, Eckhard Wöstefeld
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AmineC‐Hfunctionalisation:partII
With Igor Jurberg, Bo Peng, Eckhard Wöstefeld and Maximilian Wasserloos, : Angew. Chem. Int. Ed. 2012, 51, 1950Angew. Chem. 2012, 124, 1986. (Hot Paper)
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TotalSynthesisofIndolizidine167B
200 mg prepared in a single run
With Igor Jurberg, Bo Peng, Eckhard Wöstefeld and Maximilian Wasserloos, : Angew. Chem. Int. Ed. 2012, 51, 1950Angew. Chem. 2012, 124, 1986. (Hot Paper)
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Conclusions
Amide activation methodologies
Development of a new Claisen‐like rearrangement
Versatile platform for the stereoselective synthesis of allyl and allenyl lactones
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New avenues in Sulfur (IV) chemistry
Unconventional acess to and reactivity of sulfur ylides
Conclusions
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New avenues in Sulfur (IV) chemistry
Direct arylations with sulfoxides
Conclusions
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Conclusions
Part II: Organic Redox‐neutral reactions
Three‐stage amine C‐H functionalisation
Total Synthesis of Indolizidine 167B
Conclusions
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Dr. Claire MadelaineViviana ValerioMaria Teresa OliveiraDr. Marco LupariaDr. Xueliang HuangDr. Davide AudisioDesislava PetkovaCaroline SourisSebastian KlimczykDr. Igor JurbergDr. Bo PengDr. Anais JolitMartina DrescherPatricia EmbergerVeronica Tona
Eckhard WöstefeldDr. Danny GeerdinkDr. Mohan PadmanabanDr. Daniel O‘DonovanRik OostSupaporn NiyomchonSaad ShaabanGerlinde GiessnerMartin BergerDr. Langui XieDr. Antonio MisaleDr. Aurélien de la TorreJuliette SabbataniDaniel Kaiser
Acknowledgement:TheMaulideGroup