Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2014; 46(18): 2506-2514
DOI: 10.1055/s-0033-1338629
DOI: 10.1055/s-0033-1338629
paper
A Novel Route to 6-Substituted Piperidin-3-ols via Domino Cyclization of 2-Hydroxy-6-phosphinyl-5-hexenyl Tosylates with Primary Amines: Synthesis of (±)-Pseudoconhydrine and (±)-epi-Pseudoconhydrine
Further Information
Publication History
Received: 02 March 2014
Accepted after revision: 04 April 2014
Publication Date:
23 June 2014 (online)
Abstract
2-Hydroxy-6-phosphinyl-5-hexenyl tosylates, oxirane ring-opening products derived from glycidyl tosylates and phosphinyl-substituted allyl anions, undergo domino SN2–Michael reactions with primary amines to give 6-phosphinylmethylpiperidin-3-ols. The phosphinyl unit can be used in Horner olefination reactions. This approach is applied to the synthesis of racemic pseudoconhydrine and its epimer.
-
References
- 1 Weintraub PM, Sabol JS, Kane JM, Borcherding DR. Tetrahedron 2003; 59: 2953
- 2 Buffat MG. P. Tetrahedron 2004; 60: 1701
- 3a De Risi C, Fanton G, Pollini GP, Trapella C, Valente F, Zanirato V. Tetrahedron: Asymmetry 2008; 19: 131
- 3b Bailey PD, Millwood PA, Smith PD. Chem. Commun. 1998; 633
- 3c Laschat S, Dickner T. Synthesis 2000; 1781
- 3d Cossy J. Chem. Rec. 2005; 5: 70
- 4 Wijdeven MA, Willemsen J, Rutjes FP. J. T. Eur. J. Org. Chem. 2010; 2831
- 5 Wijdeven MA, van Delft FL, Rutjes FP. J. T. Tetrahedron 2010; 66: 5623
- 6a Christofidis I, Welter A, Jadot J. Tetrahedron 1977; 33: 977
- 6b Hasseberg H.-A, Gerlach H. Liebigs Ann. Chem. 1989; 255
- 6c Makabe H, Kong LK, Mitsuru H. Org. Lett. 2003; 5: 27
- 7a Toyooka N, Yoshida Y, Yotsui Y, Momose T. J. Org. Chem. 1999; 64: 4914
- 7b Kim IS, Ryu CB, Li QR, Zee OP, Jung YH. Tetrahedron Lett. 2007; 48: 6258
- 8 Kazmaier U, Grandel R. Eur. J. Org. Chem. 1998; 1833
- 9 Ibekeke-Bomangwa W, Hootelé C. Tetrahedron 1987; 43: 935
- 10 Ladenburg A, Adam G. Ber. Dtsch. Chem. Ges. 1891; 24: 1671
- 11a Marion L, Cockburn WF. J. Am. Chem. Soc. 1949; 71: 3402
- 11b Gruber W, Schlögl K. Monatsh. Chem. 1949; 80: 499
- 11c Šorm F, Sicher J. Collect. Czech. Chem. Commun. 1949; 14: 331
- 11d Brown E, Lavoue J, Dhal R. Tetrahedron 1973; 29: 455
- 11e Enders D, Hassel T, Pieter R, Renger B, Seebach D. Synthesis 1976; 548
- 11f Renger B, Kalinowski H.-O, Seebach D. Chem. Ber. 1977; 110: 1866
- 11g Shono T, Matsumura Y, Onomura O. Chem. Lett. 1984; 1101
- 11h Harding KE, Burks SR. J. Org. Chem. 1984; 49: 40
- 11i Plehiers M, Hootelé C. Tetrahedron Lett. 1993; 34: 7569
- 11j Fry DF, Brown M, McDonald JC. Tetrahedron Lett. 1996; 37: 6227
- 11k Plehiers M, Hootelé C. Can. J. Chem. 1996; 74: 2444
- 12a Tadano K, Iimura Y, Suami T. J. Carbohydr. Chem. 1985; 4: 129
- 12b Takahata H, Inose K, Momose T. Heterocycles 1994; 38: 269
- 12c Oppolzer W, Bochet CG. Tetrahedron Lett. 1995; 36: 2959
- 12d Herdeis C, Held WA, Kirfel A, Schwabenländer F. Liebigs Ann. 1995; 1295
- 12e Sakagami H, Kamikubo T, Ogasawara K. Chem. Commun. 1996; 1433
- 12f Hirai Y, Shibuya K, Fukuda Y, Yokoyama H, Yamaguchi S. Chem. Lett. 1997; 221
- 12g Dockner M, Sasaki NA, Riche C, Potier P. Liebigs Ann. Recl. 1997; 1267
- 12h Moody CJ, Lightfoot AP, Gallagher PT. J. Org. Chem. 1997; 62: 746
- 12i Cossy J, Dumas C, Pardo DG. Synlett 1997; 905
- 12j Herdeis C, Schiffer T. Synthesis 1997; 1405
- 12k Agami C, Couty F, Lam H, Mathieu H. Tetrahedron 1998; 54: 8783
- 12l Löfstedt J, Pettersson-Fasth H, Bäckvall J.-E. Tetrahedron 2000; 56: 2225
- 12m Hedley SJ, Moran WJ, Prenzel AH. G. P, Price DA, Harrity JP. A. Synlett 2001; 1596
- 12n Liu G, Meng J, Feng C.-G, Huang P.-Q. Tetrahedron: Asymmetry 2008; 19: 1297
- 12o Satyalakshmi G, Suneel K, Shinde DB, Das B. Tetrahedron: Asymmetry 2011; 22: 1000
- 12p Bates RW, Sivarajan K, Straub BF. J. Org. Chem. 2011; 76: 6844
- 12q Higashiyama K, Matsumura M, Kurita E, Yamauchi T. Heterocycles 2012; 86: 371
- 12r Lovick HM, Michael FE. J. Am. Chem. Soc. 2010; 132: 1249
- 13 Ergüden J.-K, Schaumann E. Synthesis 1996; 707
- 14 Bunce RA, Peeples CJ, Jones PB. J. Org. Chem. 1992; 57: 1727
- 15 Bryson TA, Smith DC, Krueger SA. Tetrahedron Lett. 1977; 525
- 16 Unit cell parameters: a = 1145.5(1) pm, b = 851.1(1) pm, c = 3014.2(1) pm, β = 102.49(1)°, V = 2869·106 pm3, Z = 4, monoclinic, space group P21/c, R = 0.059, Rw = 0.147. CCDC 799120 contains the supplementary crystallographic data for this compound. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
- 17a Czech B, Bartsch RA. J. Org. Chem. 1984; 49: 4076
- 17b Sajiki H, Kuno H, Hirota K. Tetrahedron Lett. 1998; 39: 7127
- 18 Gao Y, Hanson RM, Klunder JM, Ko SY, Masamune H, Sharpless KB. J. Am. Chem. Soc. 1987; 109: 5765
- 19 Nakabayashi N, Masuhara E, Iwakura Y. Bull. Chem. Soc. Jpn. 1966; 39: 413
- 20 Inman M, Moody CJ. J. Org. Chem. 2010; 75: 6023