Subscribe to RSS
DOI: 10.1055/s-0028-1083325
Intermolecular Addition Reactions of N-Acyliminium Ions (Part I) [¹]
Publication History
Publication Date:
26 January 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200903/lookinside/thumbnails/10.1055-s-0028-1083325-1.jpg)
Abstract
This review highlights the advances in the literature up to July 2008 on the intermolecular reactions of acyclic and cyclic N-acyliminium ions. This is an update of an earlier review in 2000 on this topic and does not include intramolecular addition reactions to N-acyliminium ions which was recently reviewed. This review is presented in two parts, with the first part dealing with acyclic and pyrrolidinone-based N-acyliminium ions. Part II continues with other five-membered heterocyclic derivatives and higher systems.
Part I
1 Introduction
2 Acyclic N-Acyliminium Ions
2.1 Synthesis of Acyclic N-Acyliminium Ion Precursors
2.2 Reactions of Acyclic N-Acyliminium Ions
2.2.1 Reactions with Nucleophiles
2.2.1.1 Silicon-Based Nucleophiles
2.2.1.2 Aromatic Nucleophiles
2.2.1.3 Organostannanes
2.2.1.4 Organometallic Reagents
2.2.1.5 Thiols
2.2.1.6 Alkenes
2.2.1.7 Nitrogen Nucleophiles
2.2.1.8 Alkyl Radicals
2.2.2 Cycloaddition Reactions
2.2.3 Cationic Carbohydroxylation Reactions
3 Cyclic N-Acyliminium Ions
3.1 Synthesis of Cyclic N-Acyliminium Ion Precursors
3.1.1 Preparation of Iminium Ions in situ by Anodic Oxidation
3.2 Five-Membered-Ring N-Acyliminium Ions
3.2.1 Reactions of Pyrrolidinone-Based N-Acyliminium Ions
3.2.1.1 Silicon-Based Nucleophiles
3.2.1.2 Aromatic Nucleophiles
3.2.1.3 Organostannanes
3.2.1.4 Organometallic Reagents
3.2.1.5 Active Methylene Compounds
3.2.1.6 Nitrile Nucleophiles (Ritter Reaction)
Part II
3.2.2 Reactions of N-Acylpyrrolidine-Based N-Acyliminium Ions with Nucleophiles
3.2.3 Reactions of Oxazolidinone-Based N-Acyliminium Ions with Nucleophiles
3.2.4 Cyclocondensation Reaction of N-Aminidinyl Iminium Ions
3.3 Reactions of Six-Membered-Ring N-Acyliminium Ions
3.3.1 Reactions of Piperidinone-Based N-Acyliminium Ions with Nucleophiles
3.3.3 Reactions of Piperazine-Based N-Acyliminium Ions with Nucleophiles
3.3.4 Reactions of Pyridine-Based N-Acyliminium Ions with Nucleophiles
3.3.5 Reactions of N,O-Acetal Oxathiazinane N-Sulfonyliminium Ions with Nucleophiles
3.4 Reactions of Seven-Membered-Ring N-Acyliminium Ions
3.4.1 Reactions with Silicon-Based Nucleophiles
3.4.2 Cycloaddition Reactions
3.5 Reactions of Bicyclic N-Acyliminium Ions
3.5.1 Reactions with Nucleophiles
3.5.2 Cycloaddition Reactions
3.6 Other Systems
3.6.1 Silicon-Based Nucleophiles
4 Stereochemical Outcomes
5 Conclusions
Key words
N-acyliminium ion - nucleophilic addition - cycloaddition - aromatic electrophilic substitution - radical addition - peptides - pyrrolidines - piperidines
- 1 For Part II, see:
Yazici A.Pyne SG. Synthesis 2009, 513 - 2
Speckamp WN.Moolenaar MJ. Tetrahedron 2000, 56: 3817 - 3
Maryanoff BE.Zhang HC.Cohen JH.Turchi IJ.Maryanoff CA. Chem. Rev. 2004, 104: 1431 - 4
Petrini M.Torregiani E. Synthesis 2007, 159 - 5
van Maarseveen JH.Meester WJN.Veerman JJN.Kruse CG.Hermkens PHH.Rutjes FPJT.Hiemstra H. J. Chem. Soc., Perkin Trans. 1 2001, 994 - 6
Meester WJN.van Maarseveen JH.Kirchsteiger K.Hermkens PHH.Schoemaker HE.Hiemstra H.Rutjes FPJT. ARKIVOC 2004, (ii): 122 - 7
Suga S.Nagaki A.Yoshida J.-i. Chem. Commun. 2003, 354 - 8
Suga S.Tsutsui Y.Nagaki A.Yoshida J.-i. Bull. Chem. Soc. Jpn. 2005, 78: 1206 - 9
Nagaki A.Togai M.Suga S.Aoki N.Mae K.Yoshida J. J. Am. Chem. Soc. 2005, 127: 11666 - 10
Petrini M.Torregiani E. Tetrahedron Lett. 2005, 46: 5999 - 11
Bergeot O.Corsi C.Qacemi ME.Zard SZ. Org. Biomol. Chem. 2006, 4: 278 - 12
Mecozzi T.Petrini M. J. Org. Chem. 1999, 64: 8970 - 13
Pearson WH.Lindbeck AC.Kampf JW. J. Am. Chem. Soc. 1993, 115: 2622 - 14
Katritzky AR.Urogdi L.Mayence A. J. Org. Chem. 1990, 55: 2206 - 15
Katritzky AR.Manju K.Singh SK.Meher NK. Tetrahedron 2005, 61 2555 - 16
Shono T.Matsumura Y.Tsubata K. J. Am. Chem. Soc. 1981, 103: 1172 - 17
Chevallier F.Beaudet I.Le Grognec E.Toupet L.Quintard J.-P. Tetrahedron Lett. 2004, 45: 761 - 18
Marshall JA.Gill K.Seletsky BM. Angew. Chem. Int. Ed. 2000, 39: 953 - 19
Wang D.-H.Hao X.-S.Wu D.-F.Yu J.-Q. Org. Lett. 2006, 8: 3387 - 20
Suh Y.-G.Shin D.-Y.Jung J.-K.Kim S.-H. Chem. Commun. 2002, 1064 - 21
DeNinno MP.Eller C.Etienne JB. J. Org. Chem. 2001, 66: 6988 - 22
Yaouancq L.Rene L.Dau M.-ETH.Badet B. J. Org. Chem. 2002, 76: 5408 - 23
Wim JN.van Dijk R.van Maarseveen JH.Rutjes FPJT.Hermkens PHH.Hiemstra H. J. Chem. Soc., Perkin Trans. 1 2001, 2909 - 24
Sun H.Martin C.Kesselring D.Keller R.Moeller KD. J. Am. Chem. Soc. 2006, 128: 13761 - 25
Suga S.Nishida T.Yamada D.Nagaki A.Yoshida J. J. Am. Chem. Soc. 2004, 126: 14338 - 26
Nilson MG.Funk RL. Org. Lett. 2006, 8: 3833 - 27
Sun H.Moeller KD. Org. Lett. 2003, 5: 3189 - 28
Sun H.Moeller KD. Org. Lett. 2002, 4: 1547 - 29
Sugiura M.Hagio H.Hirabayashi R.Kobayashi S. J. Am. Chem. Soc. 2001, 123: 12510 -
30a
Mentink G.Van Maarseveen JH.Hiemstra H. Org. Lett. 2002, 4: 3497 -
30b
Berkheij M.Dijkink J.David ORP.Sonke T.Ijzendoorn DR.Blaauw RH.Van Maarseveen JH.Schoemaker HE.Hiemstra H. Eur. J. Org. Chem. 2008, 914 - 31
Giardina A.Mecozzi T.Petrini M. J. Org. Chem. 2000, 65: 8277 - 32
Shin D.-Y.Jung J.-K.Seo S.-Y.Lee Y.-S.Paek S.-M.Chung YK.Shin DM.Suh Y.-G. Org. Lett. 2003, 5: 3635 - 33
Marcantoni E.Mecozzi T.Petrini M. J. Org. Chem. 2002, 67: 2989 - 34
Ballini R.Palmeieri A.Petrini M.Torregiani E. Org. Lett. 2006, 8: 4093 - 35
Kuhakarn C.Tangdenpaisal K.Kongsaeree P.Prabpai S.Tuchinda P.Pohmakotr M.Reutrakul V. Tetrahedron Lett. 2007, 48: 2467 - 36
Zhang Y.DeSchepper DJ.Gilbert TM.Kumar KSS.Klumpp DA. Chem. Commun. 2007, 4032 - 37
Mecozzi T.Petrini M.Profeta R. Tetrahedron: Asymmetry 2003, 14: 1171 - 38
Suga S.Okajima M.Yoshida J.-i. Tetrahedron Lett. 2001, 42: 2173 - 39
Roy B.Perez-Luna A.Ferreira F.Botuha C.Chemla F. Tetrahedron Lett. 2008, 49: 1534 - 40
Nagaki A.Kawamura K.Suga S.Ando T.Sawamoto M.Yoshida J. J. Am. Chem. Soc. 2004, 126: 14702 - 41
Maruyama T.Suga S.Yoshida J.-i. Tetrahedron 2006, 62: 6519 - 42
Maruyama T.Suga S.Yoshida J. J. Am. Chem. Soc. 2005, 127: 7324 - 43
Suga S.Nagaki A.Tsutsui Y.Yoshida J. Org. Lett. 2003, 5: 945 - 44
Suga S.Kageyama Y.Babu G.Itami K.Yoshida J.-I. Org. Lett. 2004, 6: 2709 - 45
Koseki Y.Kusano S.Ichi D.Yoshida K.Nagasaka T. Tetrahedron 2000, 56: 8855 - 46
Boto A.Hernandez R.Suarez E. J. Org. Chem. 2000, 65: 4930 - 47
Boto A.Hernandez R.Suarez E. Tetrahedron Lett. 2000, 41: 2899 - 48
Chai CLL.Elix JA.Huleatt PB. Tetrahedron 2005, 61: 8722 - 49
Kim S.Hayashi K.Kitano Y.Tada M.Chiba K. Org. Lett. 2002, 4: 3735 - 50
Maruyama T.Mizuno Y.Shimizu I.Suga S.Yoshida J.-i. J. Am. Chem. Soc. 2007, 129: 1902 - 51
Karstens WFJ.Klomp D.Rutjes FPJT.Hiemstra H. Tetrahedron 2001, 57: 5123 - 52
Ronaldo A.Robello LG. Synlett 2005, 2297 - 53
Godfrey CRA.Simpkins NS.Walker MD. Synlett 2000, 388 - 54
Ben Othman R.Bousquet T.Fousse A.Othman M.Dalla V. Org. Lett. 2005, 7: 2825 - 55
Ben Othman R.Bousquet T.Othman M.Dalla V. Org. Lett. 2005, 7: 5335 - 56
Baussanne I.Chiaroni A.Royer J. Tetrahedron: Asymmetry 2001, 12: 1219 - 57
Kende AS.Hernando J. I. M.Milbank JBJ. Tetrahedron 2002, 58: 61 - 58
Kende AS.Hernando JI. M.Milbank JB. J. Org. Lett. 2001, 3: 2505 - 59
Oba M.Mita A.Kondo Y.Nishiyama K. Synth. Commun. 2005, 35: 2961 - 60
Lennartz M.Steckhan E. Synlett 2000, 319 - 61
Andrade CKZ.Rocha RO.Russowsky D.Godoy MN. J. Braz. Chem. Soc. 2005, 16: 535 - 62
Pin F.Comesse S.Garrigues B.Marchalin S.Daiech A. J. Org. Chem. 2007, 72: 1181 - 63
Tranchant M.-J.Moine C.Ben Othman R.Bousquet T.Othman M.Dalla V. Tetrahedron Lett. 2006, 47: 4477 -
64a
Morgan IR.Yazici A.Pyne SG. Tetrahedron 2008, 64: 1409 -
64b
Unpublished results from these laboratories.
-
65a
Zhou X.Liu W.-J.Ye J.-L.Huang P.-Q. J. Org. Chem. 2007, 72: 8904 -
65b
Zhou X.Huang P.-Q. Synlett 2006, 1235 - 66
Dai C.-F.Cheng F.Xu H.-C.Ruan Y.-P.Huang P.-Q. J. Comb. Chem. 2007, 9: 386 - 67
Jeong HJ.Lee JM.Kim MK.Lee S.-G. J. Heterocycl. Chem. 2002, 39: 1019 - 68
Schuch CM.Pilli RA. Tetrahedron: Asymmetry 2002, 13: 1973 - 69
Huang J.-M.Hong S.-C.Wu K.-L.Tsai Y.-M. Tetrahedron Lett. 2004, 45: 3047 - 70
Klitzke CF.Pilli RA. Tetrahedron Lett. 2001, 42: 5605 - 71
Oba M.Koguchi S.Nishiyama K. Tetrahedron 2002, 58: 9359 - 72
Zhou X.Liu W.-J.Ye J.-L.Huang P.-Q. Tetrahedron 2007, 63: 6346 - 73
Schuch CM.Pilli RA. Tetrahedron: Asymmetry 2000, 11: 753 - 74
Muramatsu T.Yamashita S.Nakamura Y.Suzuki M.Mase N.Yoda H.Takabe K. Tetrahedron Lett. 2007, 48: 8956 - 75
Ostendorf M.Dijkink J.Rutjes FPJT.Hiemstra H. Eur. J. Org. Chem. 2000, 115 - 76
Yoda H.Egawa T.Takabe K. Tetrahedron Lett. 2003, 44: 1643 - 77
Washburn DG.Heidebrecht R.Martin SF. Org. Lett. 2003, 5: 3523 - 78
Huang P.-Q.Tang X.Chen AQ. Synth. Commun. 2000, 30: 2259 - 79
Vieira AS.Ferreira FP.Fiorante PF.Guadagnin RC.Stefani HA. Tetrahedron 2008, 64: 3306 - 80
Morgan IR.Yazici A.Pyne SG.Skelton BW. J. Org. Chem. 2008, 73: 2943