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 2015; 47(17): 2497-2522
DOI: 10.1055/s-0034-1378863
DOI: 10.1055/s-0034-1378863
review
Stereoselective Reactions in Preparation of Chiral α-Heteraspiro[m.n]alkanes
Weitere Informationen
Publikationsverlauf
Received: 05. Mai 2015
Accepted after revision: 23. Juni 2015
Publikationsdatum:
05. August 2015 (online)
Abstract
The biological importance and wide occurrence of spirane systems in nature have stimulated studies in spirane chemistry. The fundamental spirane framework consists of two monocyclic rings linked in an orthogonal relationship by a common ring carbon. This review covers families of annular α-monoheteraspiranes starting with α-heteraspiro[2.4]heptanes and terminating with α-hetera[5.6]dodecanes; the annular heteroatoms are N, O, or S. The spirane systems are arranged according to the relative size of the two monocyclic rings with highest priority for the smaller ring, Often optically active spiranes are prepared for biological reasons by chemical modifications of natural products related to the spirane to be prepared. Chiral auxiliaries are useful in the introduction and control of stereochemistry in the construction of spiranes as intermediates in the preparation of novel amino acids and nucleosides. Another aspect of chiral spirane chemistry concerns modifications and conformational restrictions introduced in natural carbohydrates, nucleosides, and amino acids.
1 Introduction
2 Heteraspira[2.m]alkanes
3 Heteraspira[3.m]alkanes
4 Heteraspira[4.m]alkanes
5 Heteraspira[5.m]alkanes
-
References
- 1 Undheim K. Synthesis 2014; 46: 1957
- 2 Cala L, Fananás FJ, Rodríguez F. Org. Biomol. Chem. 2014; 12: 5324
- 3 Palmes JA, Aponick A. Synthesis 2012; 44: 3699
- 4 Sannigrahi M. Tetrahedron 1999; 55: 9007
- 5 Grygorenko OO, Radchenko DS, Volochnyuk DM, Tolmachev AA, Komarov IV. Chem. Rev. 2011; 111: 5506
- 6 Kohta S, Deb AC, Lahiri K, Manivannan E. Synthesis 2009; 165
- 7 Aburel PS, Rømming C, Ma K, Undheim K. J. Chem. Soc., Perkin Trans. 1 2001; 1458
- 8 Undheim K. Amino Acids 2008; 34: 357
- 9 Paquette LA. Aust. J. Chem. 2004; 57: 7
- 10 Dake G. Tetrahedron 2006; 62: 3467
- 11 Fitzi R, Seebach D. Tetrahedron 1988; 44: 5277
- 12 Seebach D, Dziadulewics E, Berendt L, Cantoreggi S, Fitzi R. Liebigs Ann. Chem. 1989; 1215
- 13 Schöllkopf U, Hupfeld B, Kuper S, Egert E, Dyrbusch M. Angew. Chem. 1988; 100: 438
- 14 Schöllkopf U, Hauptreif M, Dippel J, Nieger M, Ernst E. Angew. Chem. 1986; 98: 187
- 15 Subramanian PK, Woodard RW. J. Org. Chem. 1987; 52: 15
- 16 Bull SD, Davies SG, Epstein SW, Ouzman VA. Chem. Commun. 1998; 659
- 17 Bunuel E, Bull SD, Davies SG, Garner AC, Savory ED, Smith AD, Vickers RJ, Watkin DJ. Org. Biomol. Chem. 2003; 1: 2531
- 18 Campbell MM, Horwell DC, Mahon MF, Pritchard MC, Walfond SP. Bioorg. Med. Chem. Lett. 1993; 3: 667
- 19 Williams RM, Im M.-N. J. Am. Chem. Soc. 1991; 113: 9276
- 20 Williams RM, Fegley GJ. J. Am. Chem. Soc. 1991; 113: 8796
- 21 Roy A, Achari B, Mandal SB. Tetrahedron Lett. 2006; 47: 3875
- 22 Maity JK, Gghosh R, Drew MG. B, Achari B, Mandal SB. J. Org. Chem. 2008; 73: 4305
- 23 Sayago FJ, Pradera MÁ, Gasch C, Fuentes J. Tetrahedron 2006; 62: 915
- 24 Babu BR, Keinicke L, Petersen M, Nielsen C, Wengel J. Org. Biomol. Chem. 2003; 1: 3514
- 25 Nagasaka T, Sato H, Saeki S.-I. Tetrahedron: Asymmetry 1997; 8: 191
- 26 Planas L, Pérard-Viret J, Boyer J. J. Org. Chem. 2004; 69: 3087
- 27 Hartung R, Paquette LA. J. Org. Chem. 2005; 70: 1597
- 28 Paquette LA, Owen DR, Bibart RT, Seekamp CK, Kahane AL, Lanter JC, Corral MA. J. Org. Chem. 2001; 66: 2828
- 29 Paquette LA, Seekamp CK, Kahane AL. J. Org. Chem. 2003; 68: 8614
- 30 Paquette LA, Bibart RT, Seekamp CK, Kahane AL. Org. Lett. 2001; 3: 4039
- 31 Maity JK, Achari B, Drew MG. B, Mandal SB. Synthesis 2010; 2533
- 32 Paquette LA, Dong S. J. Org. Chem. 2005; 70: 5655
- 33 Sano H, Sugai S. Tetrahedron: Asymmetry 1995; 6: 1143
- 34 Sano H, Sugai S. Tetrahedron 1995; 51: 4635
- 35 Pham TQ, Pyne SG, Skelton BW, White AH. J. Org. Chem. 2005; 70: 6369
- 36 Gasch C, Merino-Montiel P, López Ó, Fernandez-Bolanos JG, Fuentes J. Tetrahedron 2010; 69: 9964
- 37a Liang H, Ciufolini MA. Chem. Eur. J. 2010; 16: 13262
- 37b Liang H, Ciufolini MA. Tetrahedron 2010; 66: 5884
- 38 Wardrop DJ, Burge MS, Zhang W, Ortíz JA. Tetrahedron Lett. 2003; 44: 2587
- 39 Snider BB, Lin H, Foxman BM. J. Am. Chem. Soc. 1999; 121: 7778
- 40 De Sousa AL, Pilli RA. Org. Lett. 2005; 7: 1617
- 41 Dake GR, Fenster MD. B, Hurley PB, Patrick BO. J. Org. Chem. 2004; 69: 5668
- 42 Dake GR, Fenster MD. B, Fleury M, Patrick BO. J. Org. Chem. 2004; 69: 5676
- 43 Jiao Z.-W, Zhang S.-Y, He C, Tu Y.-Q, Wang S.-H, Zhang F.-M, Zhang Y.-Q, Li H. Angew. Chem. Int. Ed. 2012; 51: 8811
- 44 Alonso D, Font J, Ortuno RM, d’Angelo J, Guingant A, Bois C. Tetrahedron 1991; 47: 5895
- 45 Sancibrao P, Gori D, Kouklovsky C, Vincent G. Chem. Eur. J. 2013; 19: 5557
- 46 Carreras J, Avenoza A, Busto JH, Peregrina JM. J. Org. Chem. 2011; 76: 3381
- 47 Andrei M, Undheim K. Tetrahedron: Asymmetry 2004; 15: 53
- 48 Möller B, Undheim K. Tetrahedron 1998; 54: 5789
- 49 Möller B, Undheim K. Eur. J. Org. Chem. 2003; 332
- 50 Hammer K, Undheim K. Tetrahedron 1997; 53: 2309
- 51 Undheim K, Efskind J. Tetrahedron 2000; 56: 4847
- 52 Hammer K, Undheim K. Tetrahedron 1997; 53: 10603
- 53 Efskind J, Rømming C, Undheim K. J. Chem. Soc., Perkin Trans. 1 2001; 2697
- 54 Efskind J, Undheim K. Tetrahedron Lett. 2003; 44: 2837
- 55 Hoven GB, Efskind J, Rømming C, Undheim K. J. Org. Chem. 2002; 67: 2459
- 56 Wang J, Falck-Pedersen ML, Rømming C, Undheim K. Synth. Commun. 2001; 31: 1141
- 57 Kulagowski JJ, Curtis NR, Swain CJ, Williams BJ. Org. Lett. 2001; 3: 667
- 58 Sahabuddin S, Roy A, Drew MG. B, Roy BG, Achari B, Mandal SB. J. Org. Chem. 2006; 71: 5980
- 59 Gupta S, Das BC, Schafmeister CE. Org. Lett. 2005; 7: 2861
- 60 Hartwig W, Mittendorf J. Synthesis 1991; 939
- 61 Tai VW.-F, Garrido D, Price DU. J, Maynard AQ, Pouliot JJ, Xiong Z, Seal III JW, Creech KL, Kryn LH, Baughman TM, Peat AJ. Bioorg. Med. Chem. Lett. 2014; 24: 2288
- 62 Sano H, Mio S, Kitagawa J, Sugai S. Tetrahedron: Asymmetry 1994; 5: 2233
- 63 Williams RM, Fegley GJ. Tetrahedron Lett. 1992; 33: 6755
- 64 Tripathi S, Roy BG, Drew MG. B, Achari B, Mandal SB. J. J. Org. Chem. 2007; 72: 7427
- 65 Wardrop DJ, Zhang W, Landrie CL. Tetrahedron Lett. 2004; 45: 4229
- 66 Hammer K, Undheim K. Tetrahedron 1997; 53: 5925
- 67 Krikstolaityté S, Hammer K, Rømming C, Undheim K. Synth. Commun. 2002; 32: 571
- 68 Krikstolaityté S, Hammer K, Undheim K. Tetrahedron Lett. 1998; 39: 7595
- 69 Hammer K, Rømmimg C, Undheim K. Tetrahedron 1998; 54: 10837
- 70 Efskind J, Hope H, Undheim K. Eur. J. Org. Chem. 2002; 464
- 71 Efskind J, Rømming C, Undheim K. J. Chem. Soc., Perkin Trans. 1 1999; 1677