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Synthesis 2014; 46(23): 3268-3272
DOI: 10.1055/s-0034-1378663
DOI: 10.1055/s-0034-1378663
paper
An Efficient Synthesis of 3,3′-Bipiperidines Using an ROM/RCM Metathesis Sequence: Extension to Oxygenated Analogues
Weitere Informationen
Publikationsverlauf
Received: 14. März 2014
Accepted after revision: 18. Juli 2014
Publikationsdatum:
28. August 2014 (online)
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Dedicated to the memory of Dr. Hans Greuter
Abstract
A short and efficient diastereoselective synthesis of 3,3′-bipiperidine and 3,3′-bis(1,2,3,6-tetrahydropyridine) was accomplished using a tandem ring-opening metathesis/ring-closing metathesis (ROM/RCM) sequence as a key step. This strategy has been extended to the synthesis of the oxygenated analogues.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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References
- 1a Mateeva NN, Winfield LL, Redda KK. Curr. Med. Chem. 2005; 12: 551
- 1b Watson PS, Jiang B, Scott B. Org. Lett. 2000; 2: 3679
- 1c Berggren K, Vindebro R, Bergstrom C, Spoerry C, Persson H, Fex T, Kihlberg J, von Pawel-Rammingen U, Luthmant K. J. Med. Chem. 2012; 55: 2549
- 1d Ortiz GX. Jr, Kang B, Wang Q. J. Org. Chem. 2014; 79: 571
- 1e Peng Z, Wong JW, Hansen EC, Puchlopek-Dermenci AL. A, Clarke HJ. Org. Lett. 2014; 16: 860 , and references cited therein
- 2a Charette AB, Bull JA, Mousseau JJ, Pelletier G. Chem. Rev. 2012; 112: 2642
- 2b For recent synthetic efforts in this field, see: Lemire A, Charette AB. Org. Lett. 2005; 7: 2747
- 2c Boussonnière A, Ranaivondrambola T, Lebreton J, Mathé-Allainmat M. Synthesis 2010; 2456
- 2d Ranaivondrambola T, Hatton W, Felpin F.-X, Evain M, Mathé-Allainmat M, Lebreton J. Synlett 2010; 1631
- 2e Subba Reddy BV, Chaya DN, Yadav JS, Grée R. Synthesis 2012; 44: 297
- 2f Domodar K, Das B. Synthesis 2012; 44: 83
- 2g Lemonnier G, Charette AB. J. Org. Chem. 2012; 77: 5832
- 2h Duttwyler S, Lu C, Rheingold AL, Bergman RG, Ellman JA. J. Am. Chem. Soc. 2012; 134: 4064
- 2i Smout V, Peschiulli A, Verbeeck S, Herrebout W, Bultinck P, Vande Velde CM. L, Berthelot D, Meerpoel L, Maes BU. W. J. Org. Chem. 2013; 78: 9803
-
2j Ren H, Wulff WA. Org. Lett. 2013; 15: 242
- 2k Veerasamy N, Carlson EC, Collett ND, Saha M, Carter RG. J. Org. Chem. 2013; 78: 4779 ; and references cited therein
- 3 Blau F. Monatsh. Chem. 1889; 10: 375
- 4a Krumholz P. J. Am. Chem. Soc. 1953; 75: 2163
- 4b Lunn G, Sansone EB. J. Org. Chem. 1986; 51: 513
- 4c Herrmann WA, Baskakov D, Herdtweck ED, Hoffmann SD, Bunlaksananusorn T, Rampf F, Rodefeld L. Organometallics 2006; 25: 2449
- 5a Naarmann H, Beaujean M, Merényi R, Viehe HG. Polym. Bull. 1980; 2: 363
- 5b Brown SH, Crabtree RH. J. Am. Chem. Soc. 1989; 111: 2935
- 5c Krajnik P, Ferguson RR, Crabtree RH. New J. Chem. 1993; 17: 559
- 5d Denmark SE, Fu F, Lawler MJ. J. Org. Chem. 2006; 71: 1523
- 6 Noole A, Lippur K, Metsala A, Lopp M, Kanger T. J. Org. Chem. 2010; 75: 1313
- 7a Hamilton TS, Adams R. J. Am. Chem. Soc. 1928; 50: 2260
- 7b Smith CR. J. Am. Chem. Soc. 1928; 50: 1936
- 7c Efimova EI, Forostyan YN. Zh. Org. Khim. 1971; 7: 2442 ; Chem. Abstr. 1972, 76, 59394
- 8a Lescop C, Mevellec L, Huet F. J. Org. Chem. 2001; 66: 4187
- 8b Pichon C, Hubert C, Alexandre C, Huet F. Tetrahedron: Asymmetry 2000; 11: 2429
- 9a Felpin F.-X, Lebreton J. Curr. Org. Synth. 2004; 1: 83
- 9b Holub N, Blechert S. Chem. Asian J. 2007; 2: 1064
-
10a Nolan SP, Clavier H. Chem. Soc. Rev. 2010; 39: 3305
- 10b Prunet J. Eur. J. Org. Chem. 2011; 3634
- 10c Fürstner A. Chem. Commun. 2011; 6505
- 10d Cossy J, Arseniyadis S, Meyer C. Metathesis in Natural Product Synthesis . Wiley-VCH; Weinheim: 2010
- 10e Donnard M, Tschamber T, Desrat S, Hinsinger K, Eustache J. Tetrahedron Lett. 2008; 49: 1192
- 10f Jeon KO, Rayabarapu DK, Rolfe A, Volp KA, Omar I, Hanson PR. Tetrahedron 2009; 65: 4992
- 10g Malik CK, Yadav RN, Drew MG. B, Ghosh S. J. Org. Chem. 2009; 74: 1957
- 10h Nguyen NN. M, Leclère M, Stogaitis N, Fallis AG. Org. Lett. 2010; 12: 1684
- 10i Bose S, Gosh M, Gosh S. J. Org. Chem. 2012; 77: 6345 ; and references cited therein
- 11a Le D, Morandi G, Legoupy S, Montembault V, Pascual S, Fontaine L. Eur. Polym. J. 2013; 49: 972
-
11b Zuercher WJ, Hashimoto M, Grubbs RH. J. Am. Chem. Soc. 1996; 118: 6634
- 11c Zhang F, Simpkins NS, Blake AJ. Org. Biomol. Chem. 2009; 7: 1963
- 11d Tang B, Bray DC, Pattenden G, Rogers J. Tetrahedron 2010; 66: 2492
- 11e Clavier H, Broggi J, Nolan SP. Eur. J. Org. Chem. 2010; 937 ; and references cited therein
- 11f Snapper ML, Tallarico JA, Randall ML. J. Am. Chem. Soc. 1997; 119: 1478
-
11g Takao K.-i, Nanamiya R, Fukushima Y, Namba A, Yoshida K, Tadano K-i. Org. Lett. 2013; 15: 5582
-
12 Groaz E, Banti D, North M. Tetrahedron Lett. 2007; 48: 1927
- 13 Groaz E, Banti D, North M. Eur. J. Org. Chem. 2007; 3727
- 14 Gauvry N, Comoy C, Lescop C, Huet F. Synthesis 1999; 574
- 15a Tsunoda T, Otsuka J, Yamamiya Y, Itô S. Chem. Lett. 1994; 539
- 15b Sisko J, Henry JR, Weinreb SM. J. Org. Chem. 1993; 58: 4945
For a recent review on this field, see:
For related publications, see:
For an excellent recent review on this topic, see:
For recent reviews on this field, see:
For recent reviews on synthetic applications, see:
For recent representative examples, see:
For recent representative examples on ROM/RCM reaction sequence on cyclobutene-containing substrates, see: