RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2012; 44(18): 2872-2884
DOI: 10.1055/s-0031-1290387
DOI: 10.1055/s-0031-1290387
special topic
Unraveling the Synthetic Utility of the Regio- and Stereoselective Lithiation of Aziridines
Weitere Informationen
Publikationsverlauf
Received: 10. Februar 2012
Accepted after revision: 30. März 2012
Publikationsdatum:
09. Juli 2012 (online)
Abstract
The chemistry and synthetic utility of lithiated aziridines are discussed. Lithiated aziridines can be easily generated and captured by electrophiles, leading to more highly functionalized derivatives. Nitrogen dynamics and complexation phenomena play crucial roles in determining the regiochemistry of the lithiation process of aziridines and the stereochemistry of the reactions of the resulting lithiated species with electrophiles. Bench experiments combined with spectroscopic investigations and density-functional theory calculations are particularly useful in elucidating the chemistry of aziridines in their carbanionic form and in unraveling new aspects of the chemistry of aziridines.
-
References
- 1a Padwa A In Comprehensive Heterocyclic Chemistry III . Vol. 1. Katrizky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Oxford: 2008: 2
- 1b Sweeney JB In Science of Synthesis . Vol. 40a. Schaumann E, Enders D. Thieme; Stuttgart: 2008: 643
- 1c Padwa A, Murphee SS. Prog. Heterocycl. Chem. 2003; 15: 75
- 1d Sweeney JB. Chem. Soc. Rev. 2002; 31: 247
- 1e Zwanenburg B, ten Holte P. Top. Curr. Chem. 2001; 216: 93
- 1f Lindstrom UM, Somfai P. Synthesis 1998; 109
- 1g Somfai P, Ahman J. Targets Heterocycl. Syst. 1999; 3: 341
- 2a Hu XE. Tetrahedron 2004; 60: 2701
- 2b D’hooghe M, Van Speybroeck V, Waroquier M, De Kimpe N. Chem. Commun. (Cambridge) 2006; 1554
- 3 Satoh T. Chem. Rev. 1996; 96: 3303
- 4a Oxiranyl and Aziridinyl Anions as Reactive Intermediates in Synthetic Organic Chemistry, Tetrahedron Symposium-in-Print . Florio S. 2003. 59. 9683-9864
- 4b Hodgson DM, Bray CD In Aziridines and Epoxides in Organic Synthesis . Yudin AK. Wiley-VCH; Weinheim: 2006: 145
- 4c Hodgson DM, Bray CD, Humphreys PG. Synlett 2006; 1
- 4d Hodgson DM, Humphreys PG, Hughes SP. Pure Appl. Chem. 2007; 79: 269
- 4e Florio S, Luisi R. Chem. Rev. 2010; 110: 5128
- 4f Florio S, Vapriati V, Salomone A. Top. Stereochem. 2010; 26: 135
- 5a Capriati V, Florio S, Luisi R. Chem. Rev. 2008; 108: 1918
- 5b Chemla F, Vrancken E In The Chemistry of Organolithium Reagents . Rappoport Z, Marek I. Wiley; New York: 2004. 1165
- 6a Boche G, Lohrenz JC. W. Chem. Rev. 2001; 101: 697
- 6b Capriati V, Florio S. Chem.–Eur. J. 2010; 16: 4152 ; and reference cited therein
- 7a It is worth mentioning that the 1-(tert-butylsulfonyl) group is more easily removed than are arylsulfonyl groups
- 7b For 1-(tert-butylsulfonyl) deprotection, see: Sun P, Weinreb SM, Shang M. J. Org. Chem. 1997; 62: 8604
- 7c For a recent report on the N-arylsulfonyl deprotection, see: Ankner T, Hilmersson G. Org. Lett. 2009; 11: 503
- 8 Coutrot P, Elgadi A, Grison C. Heterocycles 1989; 28: 1179
- 9a Evans DA, Faul MM, Bilodeau MT. J. Am. Chem. Soc. 1994; 116: 2742
- 9b Södergren MJ, Alonso DA, Bedekar AV, Andersson PG. Tetrahedron Lett. 1997; 38: 6897
- 9c Ando T, Kano D, Minakata S, Ryu I, Komatsu M. Tetrahedron 1998; 54: 13485
- 9d Ali SI, Nikalje MD, Sudalai A. Org. Lett. 1999; 1: 705
- 9e Thakur VV, Sudalai A. Tetrahedron Lett. 2003; 44: 989
- 9f Jeong JU, Tao B, Sagasser I, Henniges H, Sharpless KB. J. Am. Chem. Soc. 1998; 120: 6844
- 10a Müller P, Nury P. Helv. Chim. Acta 2001; 84: 662
- 10b Müller P, Riegert D, Bernardinelli G. Helv. Chim. Acta 2004; 87: 227
- 11 Capriati V, Florio S, Luisi R, Musio B. Org. Lett. 2005; 7: 3749
- 12 Hodgson DM, Humphreys PG, Xu Z, Ward JG. Angew. Chem. Int. Ed. 2007; 46: 2245
- 13 Hodgson DM, Bray CD, Kindon ND. Org. Lett. 2005; 7: 2305
- 14 Musio B, Clarkson GJ, Shipman M, Florio S, Luisi R. Org. Lett. 2009; 11: 325
- 15a Hodgson DM, Hughes SP, Thompson AL, Heightman TD. Org. Lett. 2008; 10: 3453
- 15b Hodgson DM, Humphreys PG, Ward JG. Org. Lett. 2005; 7: 1153
- 16 Hodgson DM, Humphreys PG, Ward JG. Org. Lett. 2006; 8: 995
- 17 Huang J, Moore SP, O’Brien P, Whitwood AC, Gilday J. Org. Biomol. Chem. 2009; 7: 335
- 18 Beak P, Wu S, Yum EK, Jun YM. J. Org. Chem. 1994; 59: 276
- 19 Capriati V, Florio S, Luisi R, Musio B. Org. Lett. 2005; 7: 3749
- 20 Hodgson DM, Humphreys PG, Xu Z, Ward JG. Angew. Chem. Int. Ed. 2007; 46: 2245
- 21 Schmidt F, Keller F, Vedrenne E, Aggarwal VK. Angew. Chem. Int. Ed. 2009; 48: 1149
- 22 Luisi R, Giovine A, Florio S. Chem.–Eur. J. 2010; 2683
- 23 Dammacco M, Degennaro L, Florio S, Luisi R, Musio B, Altomare A. J. Org. Chem. 2009; 74: 6319
- 24 Giovine A. Ph.D. Dissertation. University of Bari; Italy: 2011
- 25 Affortunato F, Florio S, Luisi R, Musio B. J. Org. Chem. 2008; 73: 9214
- 26 Azzena U, Dettori G, Pisano L, Musio B, Luisi R. J. Org. Chem. 2011; 76: 2291
- 27 Luisi R, Capriati V, Florio S, Musio B. Org. Lett. 2007; 9: 1263
- 28 Capriati V, Florio S, Luisi R, Mazzanti A, Musio B. J. Org. Chem. 2008; 73: 3197
- 29 De Ceglie MC, Musio B, Affortunato F, Moliterno A, Florio S, Luisi R. Chem.–Eur. J. 2011; 17: 286
- 30a Bassindale AR, Ellis RJ, Lau JC.-Y, Taylor PG. J. Chem. Soc., Chem. Commun. 1986; 98
- 30b Aggarwal VK, Alonso E, Ferrara E, Spey SE. J. Org. Chem. 2002; 67: 2335
- 31 Florio S, Troisi L, Capriati V, Ingrosso G. Tetrahedron Lett. 1999; 40: 6101
- 32 Luisi R, Capriati V, Florio S, Di Cunto P, Musio B. Tetrahedron 2005; 61: 3251
- 33 Capriati V, Degennaro L, Florio S, Favia R, Luisi R. Org. Lett. 2002; 4: 1551
- 34 Luisi R, Capriati V, Di Cunto P, Florio S, Mansueto R. Org. Lett. 2007; 9: 3295
- 35 Degennaro L, Mansueto R, Carenza E, Rizzi R, Florio S, Pratt LM, Luisi R. Chem.–Eur. J. 2011; 12: 1761
- 36 Capriati V, Florio S, Luisi R, Perna FM, Spina A. J. Org. Chem. 2008; 73: 9552
- 37 Troisi L, Granito C, Carlucci C, Bona F, Florio S. Eur. J. Org. Chem. 2006; 775
- 38 Katritzky AR, Yao J, Bao W, Qi M, Steel PJ. J. Org. Chem. 1999; 64: 346
- 39 De Vitis L, Florio S, Granito C, Ronzini L, Troisi L, Capriati V, Luisi R, Pilati T. Tetrahedron 2004; 60: 1175
- 40 Luisi R, Capriati V, Florio S, Di Cunto P, Musio B. Tetrahedron 2005; 61: 3251
For recent reviews of lithiated epoxide and aziridine chemistry, see:
For reviews on the chemistry of carbenoids, see: