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(12): 1648-1658
DOI: 10.1055/s-0033-1338615
DOI: 10.1055/s-0033-1338615
paper
Imino Glycals via Ruthenium-Catalyzed RCM and Isomerization
Further Information
Publication History
Received: 11 February 2014
Accepted after revision: 06 March 2014
Publication Date:
28 March 2014 (online)
Abstract
N-Allyl-N-homoallylamines were converted in one step into cyclic enamides via a ruthenium-catalyzed assisted tandem catalytic ring-closing metathesis–isomerization sequence. The sequence relies on the in situ transformation of a metathesis active Ru–carbene into an isomerization active Ru–hydride by addition of hydroxide as a chemical trigger.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Ferrier RJ. Top. Curr. Chem. 2001; 215: 153
- 2 Ferrier RJ, Hoberg JO. Adv. Carbohydr. Chem. Biochem. 2003; 58: 55
- 3 Seeberger PH, Danishefsky SJ. Acc. Chem. Res. 1998; 31: 685
- 4 Seeberger PH, Haase WC. Chem. Rev. 2000; 100: 4349
- 5 Tolstikov AG, Tolstikov GA. Russ. Chem. Rev. 1993; 62: 579
- 6 Sun Z, Yu S, Ding Z, Ma D. J. Am. Chem. Soc. 2007; 129: 9300
- 7 Severino EA, Costenaro ER, Garcia AL. L, Correia CR. D. Org. Lett. 2003; 5: 305
- 8 Ojima I, Vidal ES. J. Org. Chem. 1998; 63: 7999
- 9 Lemire A, Charette AB. Org. Lett. 2005; 7: 2747
- 10 Cossy J. Chem. Rec. 2005; 5: 70
- 11 Furukubo S, Moriyama N, Onomura O, Matsumura Y. Tetrahedron Lett. 2004; 45: 8177
- 12 Oliveira DF, Miranda PC. M. L, Correia CR. D. J. Org. Chem. 1999; 64: 6646
- 13 Le Corre L, Kizirian J.-C, Levraud C, Boucher J.-L, Bonnet V, Dhimane H. Org. Biomol. Chem. 2008; 6: 3388
- 14 Pattenden LC, Adams H, Smith SA, Harrity JP. A. Tetrahedron 2008; 64: 2951
- 15 Chiou W.-H, Schoenfelder A, Sun L, Mann A, Ojima I. J. Org. Chem. 2007; 72: 9418
- 16 Deiters A, Martin SF. Chem. Rev. 2004; 104: 2199
- 17 Dragutan I, Dragutan V, Demonceau A. RSC Adv. 2012; 2: 719
- 18 Kinderman SS, van Maarseveen JH, Schoemaker HE, Hiemstra H, Rutjes FP. J. T. Org. Lett. 2001; 3: 2045
- 19 Arisawa M, Terada Y, Nakagawa M, Nishida A. Angew. Chem. Int. Ed. 2002; 41: 4732
- 20 Arisawa M, Terada Y, Takahashi K, Nakagawa M, Nishida A. J. Org. Chem. 2006; 71: 4255
- 21 Sturino CF, Wong JC. Y. Tetrahedron Lett. 1998; 39: 9623
- 22 Markad SD, Xia S, Snyder NL, Surana B, Morton MD, Hadad CM, Peczuh MW. J. Org. Chem. 2008; 73: 6341
- 23 Fuwa H, Naito S, Goto T, Sasaki M. Angew. Chem. Int. Ed. 2008; 47: 4737
- 24 Louie J, Grubbs RH. Organometallics 2002; 21: 2153
- 25 Sutton AE, Seigal BA, Finnegan DF, Snapper ML. J. Am. Chem. Soc. 2002; 124: 13390
- 26 Schmidt B. Eur. J. Org. Chem. 2003; 816
- 27 Schmidt B. J. Org. Chem. 2004; 69: 7672
- 28 Fogg DE, dos Santos EN. Coord. Chem. Rev. 2004; 248: 2365
- 29 Rengasamy R, Curtis-Long MJ, Seo WD, Jeong SH, Jeong IY, Park KH. J. Org. Chem. 2008; 73: 2898
- 30 Schwab P, Grubbs RH, Ziller JW. J. Am. Chem. Soc. 1996; 118: 100
- 31 Scholl M, Ding S, Lee CW, Grubbs RH. Org. Lett. 1999; 1: 953
- 32 Fürstner A, Ackermann L, Gabor B, Goddard R, Lehmann CW, Mynott R, Stelzer F, Thiel OR. Chem. Eur. J. 2001; 7: 3236
- 33 Dinger MB, Mol JC. Organometallics 2003; 22: 1089
- 34 Dinger MB, Mol JC. Eur. J. Inorg. Chem. 2003; 2827
- 35 Ulman M, Grubbs RH. J. Org. Chem. 1999; 64: 7202
- 36 Hong SH, Day MW, Grubbs RH. J. Am. Chem. Soc. 2004; 126: 7414
- 37 Higman CS, Plais L, Fogg DE. ChemCatChem 2013; 5: 3548
- 38 Schmidt B. Synlett 2004; 1541
- 39 Lawrence NJ, Drew MD, Bushell SM. J. Chem. Soc., Perkin Trans. 1 1999; 3381
- 40 Menozzi C, Dalko PI, Cossy J. Synlett 2005; 2449
- 41 Schmidt B. Chem. Commun. 2004; 742
- 42 Beach NJ, Lummiss JA. M, Bates JM, Fogg DE. Organometallics 2012; 31: 2349
- 43 Hong SH, Sanders DP, Lee CW, Grubbs RH. J. Am. Chem. Soc. 2005; 127: 17160
- 44 Fustero S, Sánchez-Roselló M, Jiménez D, Sanz-Cervera JF, del Pozo C, Aceña JL. J. Org. Chem. 2006; 71: 2706
- 45 Coombs TC, Lushington GH, Douglas J, Aubé J. Angew. Chem. Int. Ed. 2011; 50: 2734
- 46 Schmidt B, Biernat A. Chem. Eur. J. 2008; 14: 6135
- 47 Kirschning A, Bechthold AF.-W, Rohr J. Top. Curr. Chem. 1997; 188: 1
- 48 Jurczak J, Gryko D, Kobrzycka E, Gruza H, Prokopowicz P. Tetrahedron 1998; 54: 6051
- 49 Gryko D, Urbanczyk-Lipkowska Z, Jurczak J. Tetrahedron: Asymmetry 1997; 8: 4059
- 50 Mengel A, Reiser O. Chem. Rev. 1999; 99: 1191
- 51 Keck GE, Andrus MB, Romer DR. J. Org. Chem. 1991; 56: 417