Enyne Metathesis Catalyzed by Ruthenium Carbene Complexes

Carina Storm Poulsen; Robert Madsen

doi:10.1055/s-2003-36243

REVIEW

Enyne Metathesis Catalyzed by Ruthenium Carbene Complexes

Carina Storm Poulsen, Robert Madsen*
Department of Chemistry, Building 201, Technical University of Denmark, 2800 Lyngby, Denmark
Fax: +4545933968; e-Mail: rm@kemi.dtu.dk;

Abstract

Alle Artikel dieser Rubrik

Abstract

Enyne metathesis combines an alkene and an alkyne into a 1,3-diene. The first enyne metathesis reaction catalyzed by a ruthenium carbene complex was reported in 1994. This review covers the advances in this transformation during the last eight years with particular emphasis on methodology development and synthetic applications.

1 Introduction
2 Catalysts and Mechanism
3 Ring-Closing Enyne Metathesis
3.1 Metathesis of Substituted Enynes and the Influence of an Ethylene Atmosphere
3.2 Formation of Different Ring-Sizes
3.3 Tandem Metathesis Reactions
3.4 Tandem Metathesis - Cycloaddition Reactions
3.5 Metathesis of Carbohydrate-Derived Enynes
3.6 Metathesis of Amino Acid- and β-Lactam-Derived Enynes
3.7 Enyne Metathesis in Natural Product Syntheses
4 Cross Enyne Metathesis
4.1 Metathesis with Substituted Alkynes and Ethylene Gas
4.2 Metathesis with Substituted Alkynes and Alkenes
5 Concluding Remarks

Key words

alkenes - alkynes - carbene complexes - catalysis - Diels-Alder reactions - enynes - metathesis - ring closure - ruthenium - tandem reactions

Volltext

Referenzen

References

<A NAME="RE07602SS-1">1</A> Ivin KJ. Mol JC. Olefin Metathesis and Metathesis Polymerization Academic Press; San Diego: 1997.

<A NAME="RE07602SS-2">2</A> Trost BM. Acc. Chem. Res. 2002, 35: 695

For recent reviews see:

<A NAME="RE07602SS-3A">3a</A> Trnka TM. Grubbs RH. Acc. Chem. Res. 2001, 34: 18

<A NAME="RE07602SS-3B">3b</A> Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3013

<A NAME="RE07602SS-3C">3c</A> Buchmeiser MR. Chem. Rev. 2000, 100: 1565

<A NAME="RE07602SS-3D">3d</A> Jørgensen M. Hadwiger P. Madsen R. Stütz AE. Wrodnigg TM. Curr. Org. Chem. 2000, 4: 565

<A NAME="RE07602SS-3E">3e</A> Roy R. Das SK. Chem. Commun. 2000, 519

<A NAME="RE07602SS-4">4</A> Mori M. Top. Organomet. Chem. 1998, 1: 133

<A NAME="RE07602SS-5A">5a</A> Chatani N. Inoue H. Morimoto T. Muto T. Murai S. J. Org. Chem. 2001, 66 : 4433

<A NAME="RE07602SS-5B">5b</A> Chatani N. Furukawa N. Sakurai H. Murai S. Organometallics 1996, 15: 901

<A NAME="RE07602SS-5C">5c</A> Chatani N. Morimoto T. Muto T. Murai S. J. Am. Chem. Soc. 1994, 116: 6049

<A NAME="RE07602SS-5D">5d</A> Trost BM. Chang VK. Synthesis 1993, 824

<A NAME="RE07602SS-5E">5e</A> Trost BM. Tanoury GJ. J. Am. Chem. Soc. 1988, 110: 1636

<A NAME="RE07602SS-6A">6a</A> Fürstner A. Stelzer F. Szillat H. J. Am. Chem. Soc. 2001, 123: 11863

<A NAME="RE07602SS-6B">6b</A> Oi S. Tsukamoto I. Miyano S. Inoue Y. Organometallics 2001, 20: 3704

<A NAME="RE07602SS-7A">7a</A> Trost BM. Doherty GA. J. Am. Chem. Soc. 2000, 122: 3801

<A NAME="RE07602SS-7B">7b</A> Fürstner A. Szillat H. Gabor B. Mynott R. J. Am. Chem. Soc. 1998, 120: 8305

<A NAME="RE07602SS-8A">8a</A> Aubert C. Buisine O. Malacria M. Chem. Rev. 2002, 102: 813 ; in this review enyne metathesis with ruthenium carbene complexes is not discussed

<A NAME="RE07602SS-9">9</A> Katz TJ. Sivavec TM. J. Am. Chem. Soc. 1985, 107: 737

<A NAME="RE07602SS-10A">10a</A> Korkowski PF. Hoye TR. Rydberg DP. J. Am. Chem. Soc. 1988, 110: 2676

<A NAME="RE07602SS-10B">10b</A> Hoye TR. Suriano JA. Organometallics 1992, 11: 2044

<A NAME="RE07602SS-10C">10c</A> Watanuki S. Ochifuji N. Mori M. Organometallics 1995, 14: 5062

<A NAME="RE07602SS-11">11</A> Nguyen ST. Johnson LK. Grubbs RH. Ziller JW. J. Am. Chem. Soc. 1992, 114: 3974

<A NAME="RE07602SS-12">12</A> Grubbs RH. Miller SJ. Fu GC. Acc. Chem. Res. 1995, 28: 446

<A NAME="RE07602SS-13">13</A> Schwab P. Grubbs RH. Ziller JW. J. Am. Chem. Soc. 1996, 118: 100

<A NAME="RE07602SS-14">14</A> Kinoshita A. Mori M. Synlett 1994, 1020

<A NAME="RE07602SS-15">15</A> Kim S.-H. Bowden N. Grubbs RH. J. Am. Chem. Soc. 1994, 116: 10801

<A NAME="RE07602SS-16">16</A> Scholl M. Ding S. Lee CW. Grubbs RH. Org. Lett. 1999, 1: 953

<A NAME="RE07602SS-17A">17a</A> Scholl M. Trnka TM. Morgan JP. Grubbs RH. Tetrahedron Lett. 1999, 40: 2247

<A NAME="RE07602SS-17B">17b</A> Huang J. Stevens ED. Nolan SP. Peterson JL. J. Am. Chem. Soc. 1999, 121: 2674

<A NAME="RE07602SS-17C">17c</A> Ackermann L. Fürstner A. Weskamp T. Kohl FJ. Herrmann WA. Tetrahedron Lett. 1999, 40: 4787

<A NAME="RE07602SS-18">18</A> Weskamp T. Schattenmann WC. Spiegler M. Herrmann WA. Angew. Chem. Int. Ed. 1998, 37: 2490

<A NAME="RE07602SS-19A">19a</A> Louie J. Grubbs RH. Angew. Chem. Int. Ed. 2001, 40: 247

<A NAME="RE07602SS-19B">19b</A> Katayama H. Urushima H. Ozawa F. J. Organomet. Chem. 2000, 606: 16

<A NAME="RE07602SS-20A">20a</A> Fürstner A. Liebl M. Lehmann CW. Picquet M. Kunz R. Bruneau C. Touchard D. Dixneuf PH. Chem.-Eur. J. 2000, 6: 1847

<A NAME="RE07602SS-20B">20b</A> Fürstner A. Hill AF. Liebl M. Wilton-Ely JDET. Chem. Commun. 1999, 601

<A NAME="RE07602SS-20C">20c</A> Picquet M. Bruneau C. Dixneuf PH. Chem. Commun. 1998, 2249

<A NAME="RE07602SS-21">21</A> Sémeric D. Bruneau C. Dixneuf PH. Adv. Synth. Catal. 2002, 344: 585

<A NAME="RE07602SS-22">22</A> Schrock RR. Tetrahedron 1999, 55: 8141

<A NAME="RE07602SS-23">23</A> Kim S.-H. Zuercher WJ. Bowden NB. Grubbs RH. J. Org. Chem. 1996, 61: 1073

<A NAME="RE07602SS-24">24</A> Schramm MP. Reddy DS. Kozmin SA. Angew. Chem. Int. Ed. 2001, 40: 4274

<A NAME="RE07602SS-25">25</A> Schürer SC. Gessler S. Buschmann N. Blechert S. Angew. Chem. Int. Ed. 2000, 39: 3898

<A NAME="RE07602SS-26">26</A> Garber SB. Kingsbury JS. Gray BL. Hoveyda AH. J. Am. Chem. Soc. 2000, 122: 8168

<A NAME="RE07602SS-27">27</A> Van Veldhuizen JJ. Garber SB. Kingsbury JS. Hoveyda AH. J. Am. Chem. Soc. 2002, 124: 4954

<A NAME="RE07602SS-28">28</A> Sanford MS. Love JA. Grubbs RH. J. Am. Chem. Soc. 2001, 123: 6543

<A NAME="RE07602SS-29A">29a</A> Cavallo L. J. Am. Chem. Soc. 2002, 124: 8965

<A NAME="RE07602SS-29B">29b</A> Vyboishchikov SF. Bühl M. Thiel W. Chem.-Eur. J. 2002, 8: 3962

<A NAME="RE07602SS-30">30</A> Fürstner A. Ackermann L. Gabor B. Goddard R. Lehmann CW. Mynott R. Stelzer F. Thiel OR. Chem.-Eur. J. 2001, 7: 3236

<A NAME="RE07602SS-31">31</A> Kitamura T. Sato Y. Mori M. Adv. Synth. Catal. 2002, 344: 678

<A NAME="RE07602SS-32">32</A> Zuercher WJ. Scholl M. Grubbs RH. J. Org. Chem. 1998, 63: 4291

<A NAME="RE07602SS-33">33</A> Codesido EM. Castedo L. Granja JR. Org. Lett. 2001, 3: 1483

<A NAME="RE07602SS-34">34</A> Huang J. Xiong H. Hsung RP. Rameshkumar C. Mulder JA. Grebe TP. Org. Lett. 2002, 4: 2417

<A NAME="RE07602SS-35">35</A> Hoye TR. Donaldson SM. Vos TJ. Org. Lett. 1999, 1: 277

<A NAME="RE07602SS-36">36</A> Mori M. Kitamura T. Sato Y. Synthesis 2001, 654

<A NAME="RE07602SS-37">37</A> Mori M. Sakakibara N. Kinoshita A. J. Org. Chem. 1998, 63: 6082

<A NAME="RE07602SS-38">38</A> Renaud J. Graf C.-D. Oberer L. Angew. Chem. Int. Ed. 2000, 39: 3101

<A NAME="RE07602SS-39">39</A> Clark JS. Elustondo F. Trevitt GP. Boyall D. Robertson J. Blake AJ. Wilson C. Stammen B. Tetrahedron 2002, 58: 1973

<A NAME="RE07602SS-40">40</A> Choi T.-L. Grubbs RH. Chem. Commun. 2001, 2648

<A NAME="RE07602SS-41">41</A> Timmer MSM. Ovaa H. Filippov DV. van der Marel GA. van Boom JH. Tetrahedron Lett. 2001, 42: 8231

<A NAME="RE07602SS-42">42</A> Kitamura T. Mori M. Org. Lett. 2001, 3: 1161

<A NAME="RE07602SS-43">43</A> Rückert A. Eisele D. Blechert S. Tetrahedron Lett. 2001, 42: 5245

<A NAME="RE07602SS-44">44</A> Arjona O. Csákӱ AG. Murcia MC. Plumet J. Tetrahedron Lett. 2000, 41: 9777

<A NAME="RE07602SS-45">45</A> Randl S. Lucas N. Connon SJ. Blechert S. Adv. Synth. Catal. 2002, 344: 631

<A NAME="RE07602SS-46">46</A> Bentz D. Laschat S. Synthesis 2000, 1766

<A NAME="RE07602SS-47">47</A> Saito N. Sato Y. Mori M. Org. Lett. 2002, 4: 803

<A NAME="RE07602SS-48">48</A> Moreno-Mañas M. Pleixats R. Santamaria A. Synlett 2001, 1784

<A NAME="RE07602SS-49">49</A> Rosillo M. Casarrubios L. Domínguez G. Pérez-Castells J. Tetrahedron Lett. 2001, 42: 7029

<A NAME="RE07602SS-50">50</A> Banti D. North M. Adv. Synth. Catal. 2002, 344: 694

<A NAME="RE07602SS-51">51</A> Yao Q. Org. Lett. 2001, 3: 2069

<A NAME="RE07602SS-52">52</A> Micalizio GC. Schreiber SL. Angew. Chem. Int. Ed. 2002, 41: 152

<A NAME="RE07602SS-53">53</A> Heerding DA. Takata DT. Kwon C. Huffman WF. Samanen J. Tetrahedron Lett. 1998, 39: 6815

<A NAME="RE07602SS-54">54</A> Lane C. Snieckus V. Synlett 2000, 1294

<A NAME="RE07602SS-55">55</A> Guo H. Madhushaw RJ. Shen F.-M. Liu R.-S. Tetrahedron 2002, 58: 5627

<A NAME="RE07602SS-56">56</A> Rodríguez JR. Castedo L. Mascareñas JL. Chem.-Eur. J. 2002, 8: 2923

<A NAME="RE07602SS-57">57</A> Yao Q. Org. Lett. 2002, 4: 427

<A NAME="RE07602SS-58">58</A> Leeuwenburgh MA. Kulker C. Duynstee HI. Overkleeft HS. van der Marel GA. van Boom JH. Tetrahedron 1999, 55: 8253

<A NAME="RE07602SS-59">59</A> Leeuwenburgh MA. Appeldoorn CCM. van Hooft PAV. Overkleeft HS. van der Marel GA. van Boom JH. Eur J. Org. Chem. 2000, 873

<A NAME="RE07602SS-60">60</A> Clark JS. Hamelin O. Angew. Chem. Int. Ed. 2000, 39: 372

<A NAME="RE07602SS-61">61</A> Boyer F.-D. Hanna I. Ricard L. Org. Lett. 2001, 3: 3095

<A NAME="RE07602SS-62">62</A> Poulsen CS. Madsen R. J. Org. Chem. 2002, 67: 4441

<A NAME="RE07602SS-63">63</A> Marco-Contelles J. Arroyo N. Ruiz-Caro J. Synlett 2001, 652

<A NAME="RE07602SS-64">64</A> Boyer F.-D. Hanna I. Tetrahedron Lett. 2002, 43: 7469

<A NAME="RE07602SS-65">65</A> Hammer K. Undheim K. Tetrahedron 1997, 53: 10603

<A NAME="RE07602SS-66">66</A> Undheim K. Efskind J. Tetrahedron 2000, 56: 4847

<A NAME="RE07602SS-67">67</A> Efskind J. Römming C. Undheim K. J. Chem. Soc., Perkin Trans. 1 2001, 2697

<A NAME="RE07602SS-68">68</A> Kotha S. Sreenivasachary N. Eur. J. Org. Chem. 2001, 3375

<A NAME="RE07602SS-69">69</A> Barrett AGM. Baugh SPD. Braddock DC. Flack K. Gibson VC. Giles MR. Marshall EL. Procopiou PA. White AJP. Williams DJ. J. Org. Chem. 1998, 63: 7893

<A NAME="RE07602SS-70">70</A> Duboc R. Hénaut C. Savignac M. Genet J.-P. Bhatnagar N. Tetrahedron Lett. 2001, 42: 2461

<A NAME="RE07602SS-71">71</A> Kinoshita A. Mori M. J. Org. Chem. 1996, 61: 8356

<A NAME="RE07602SS-72">72</A> Kinoshita A. Mori M. Heterocycles 1997, 46: 287

<A NAME="RE07602SS-73">73</A> Clark JS. Townsend RJ. Blake AJ. Teat SJ. Johns A. Tetrahedron Lett. 2001, 42: 3235

<A NAME="RE07602SS-74">74</A> Layton ME. Morales CA. Shair MD. J. Am. Chem. Soc. 2002, 124: 773

<A NAME="RE07602SS-75">75</A> Kinoshita A. Sakakibara N. Mori M. J. Am. Chem. Soc. 1997, 119: 12388

<A NAME="RE07602SS-76">76</A> Kinoshita A. Sakakibara N. Mori M. Tetrahedron 1999, 55: 8155

<A NAME="RE07602SS-77">77</A> Smulik JA. Diver ST. J. Org. Chem. 2000, 65: 1788

<A NAME="RE07602SS-78">78</A> Vasil’ev AA. Engman L. Serebryakov EP. Mendeleev Commun. 2000, 101

<A NAME="RE07602SS-79">79</A> Smulik JA. Diver ST. Org. Lett. 2000, 2: 2271

<A NAME="RE07602SS-80">80</A> Smulik JA. Giessert AJ. Diver ST. Tetrahedron Lett. 2002, 43: 209

<A NAME="RE07602SS-81">81</A> Tonogaki K. Mori M. Tetrahedron Lett. 2002, 43: 2235

<A NAME="RE07602SS-82">82</A> Zheng G. Dougherty TJ. Pandey RK. Chem. Commun. 1999, 2469

<A NAME="RE07602SS-83">83</A> Mori M. Tonogaki K. Nishiguchi N. J. Org. Chem. 2002, 67: 224

<A NAME="RE07602SS-84">84</A> Stragies R. Schuster M. Blechert S. Angew. Chem. Int. Ed. 1997, 36: 2518

<A NAME="RE07602SS-85">85</A> Rodríguez-Conesa S. Candal P. Jiménez C. Rodríguez J. Tetrahedron Lett. 2001, 42: 6699

<A NAME="RE07602SS-86">86</A> Stragies R. Voigtmann U. Blechert S. Tetrahedron Lett. 2000, 41: 5465

<A NAME="RE07602SS-87A">87a</A> Smulik JA. Diver ST. Tetrahedron Lett. 2001, 42: 171

<A NAME="RE07602SS-87B">87b</A> Stragies R. Schuster M. Blechert S. Chem. Commun. 1999, 237

<A NAME="RE07602SS-88A">88a</A> Kotha S. Halder S. Brahmachary E. Ganesh T. Synlett 2000, 853

<A NAME="RE07602SS-88B">88b</A> Schürer SC. Blechert S. Chem. Commun. 1999, 1203

<A NAME="RE07602SS-88C">88c</A> Schürer SC. Blechert S. Tetrahedron Lett. 1999, 40: 1877

<A NAME="RE07602SS-89A">89a</A> Schuster M. Blechert S. Tetrahedron Lett. 1998, 39: 2295

<A NAME="RE07602SS-89B">89b</A> Schürer SC. Blechert S. Synlett 1998, 166

<A NAME="RE07602SS-90">90</A> Schürer SC. Blechert S. Synlett 1999, 1879