Gold(I)-Catalyzed Intramolecular Cyclopropanation of Dienynes
Gold(I) complexes are the most active catalysts for the biscyclopropanation of dienynes to form tetracyclic compounds. PtII and ZnII are also able to promote the biscyclopropanation, although less efficiently. The configurations obtained in all cases with the use of gold(I) catalysts can be explaine...
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| Published in | Chemistry : a European journal Vol. 12; no. 6; pp. 1694 - 1702 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
08.02.2006
WILEY‐VCH Verlag Wiley |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0947-6539 1521-3765 |
| DOI | 10.1002/chem.200501089 |
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| Abstract | Gold(I) complexes are the most active catalysts for the biscyclopropanation of dienynes to form tetracyclic compounds. PtII and ZnII are also able to promote the biscyclopropanation, although less efficiently. The configurations obtained in all cases with the use of gold(I) catalysts can be explained by the pathway proceeding through anti cyclopropyl gold carbenes. Similar intermediates are most probably involved in reactions catalyzed by RuII and PtII. Two different cyclopropanation pathways have been found; they depend on the structures of the cyclopropyl gold carbenes (anti or syn) and the relative arrangements of the metal carbenes and the alkenes.
Gold(I) complexes are the most active catalysts for the biscyclopropanation of dienynes to form tetracyclic compounds (see scheme): The configurations of these tetracycles can be explained by the pathway proceeding through cyclopropanation of the intermediate gold carbenes with the pendant alkene. |
|---|---|
| AbstractList | Gold(
I
) complexes are the most active catalysts for the biscyclopropanation of dienynes to form tetracyclic compounds. Pt
II
and Zn
II
are also able to promote the biscyclopropanation, although less efficiently. The configurations obtained in all cases with the use of gold(
I
) catalysts can be explained by the pathway proceeding through
anti
cyclopropyl gold carbenes. Similar intermediates are most probably involved in reactions catalyzed by Ru
II
and Pt
II
. Two different cyclopropanation pathways have been found; they depend on the structures of the cyclopropyl gold carbenes (
anti
or
syn
) and the relative arrangements of the metal carbenes and the alkenes. Gold(I) complexes are the most active catalysts for the biscyclopropanation of dienynes to form tetracyclic compounds. PtII and ZnII are also able to promote the biscyclopropanation, although less efficiently. The configurations obtained in all cases with the use of gold(I) catalysts can be explained by the pathway proceeding through anti cyclopropyl gold carbenes. Similar intermediates are most probably involved in reactions catalyzed by RuII and PtII. Two different cyclopropanation pathways have been found; they depend on the structures of the cyclopropyl gold carbenes (anti or syn) and the relative arrangements of the metal carbenes and the alkenes.Gold(I) complexes are the most active catalysts for the biscyclopropanation of dienynes to form tetracyclic compounds. PtII and ZnII are also able to promote the biscyclopropanation, although less efficiently. The configurations obtained in all cases with the use of gold(I) catalysts can be explained by the pathway proceeding through anti cyclopropyl gold carbenes. Similar intermediates are most probably involved in reactions catalyzed by RuII and PtII. Two different cyclopropanation pathways have been found; they depend on the structures of the cyclopropyl gold carbenes (anti or syn) and the relative arrangements of the metal carbenes and the alkenes. Gold(I) complexes are the most active catalysts for the biscyclopropanation of dienynes to form tetracyclic compounds. Pt-II and Zn-II are also able to promote the biscyclopropanation, although less efficiently. The configurations obtained in all cases with the use of gold(I) catalysts can be explained by the pathway proceeding through anti cyclopropyl gold carbenes. Similar intermediates are most probably involved in reactions catalyzed by Ru-II and Pt-II. Two different cyclopropanation pathways have been found; they depend on the structures of the cyclopropyl gold carbenes (anti or syn) and the relative arrangements of the metal carbenes and the alkenes. Gold(I) complexes are the most active catalysts for the biscyclopropanation of dienynes to form tetracyclic compounds. PtII and ZnII are also able to promote the biscyclopropanation, although less efficiently. The configurations obtained in all cases with the use of gold(I) catalysts can be explained by the pathway proceeding through anti cyclopropyl gold carbenes. Similar intermediates are most probably involved in reactions catalyzed by RuII and PtII. Two different cyclopropanation pathways have been found; they depend on the structures of the cyclopropyl gold carbenes (anti or syn) and the relative arrangements of the metal carbenes and the alkenes. Gold(I) complexes are the most active catalysts for the biscyclopropanation of dienynes to form tetracyclic compounds. PtII and ZnII are also able to promote the biscyclopropanation, although less efficiently. The configurations obtained in all cases with the use of gold(I) catalysts can be explained by the pathway proceeding through anti cyclopropyl gold carbenes. Similar intermediates are most probably involved in reactions catalyzed by RuII and PtII. Two different cyclopropanation pathways have been found; they depend on the structures of the cyclopropyl gold carbenes (anti or syn) and the relative arrangements of the metal carbenes and the alkenes. Gold(I) complexes are the most active catalysts for the biscyclopropanation of dienynes to form tetracyclic compounds (see scheme): The configurations of these tetracycles can be explained by the pathway proceeding through cyclopropanation of the intermediate gold carbenes with the pendant alkene. |
| Author | Muñoz, M. Paz Jiménez-Núñez, Eloísa Cárdenas, Diego J. Nieto-Oberhuber, Cristina López, Salomé Buñuel, Elena Echavarren, Antonio M. |
| Author_xml | – sequence: 1 givenname: Cristina surname: Nieto-Oberhuber fullname: Nieto-Oberhuber, Cristina organization: Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain, Fax: (+34) 977-920-225 – sequence: 2 givenname: Salomé surname: López fullname: López, Salomé organization: Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain, Fax: (+34) 977-920-225 – sequence: 3 givenname: M. Paz surname: Muñoz fullname: Muñoz, M. Paz organization: Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain – sequence: 4 givenname: Eloísa surname: Jiménez-Núñez fullname: Jiménez-Núñez, Eloísa organization: Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain, Fax: (+34) 977-920-225 – sequence: 5 givenname: Elena surname: Buñuel fullname: Buñuel, Elena organization: Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain – sequence: 6 givenname: Diego J. surname: Cárdenas fullname: Cárdenas, Diego J. organization: Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain – sequence: 7 givenname: Antonio M. surname: Echavarren fullname: Echavarren, Antonio M. email: aechavarren@iciq.es organization: Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain, Fax: (+34) 977-920-225 |
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| Keywords | SKELETAL REORGANIZATION MOLECULAR CALCULATIONS SESQUITERPENE ALCOHOL MECHANISM EFFECTIVE CORE POTENTIALS alkynes cyclization CATALYZED CYCLOISOMERIZATION REACTIONS gold density functional calculations platinum ENYNE METATHESIS X-RAY CRYSTAL zinc |
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(e_1_2_6_67_2) e_1_2_6_61_2 e_1_2_6_84_2 e_1_2_6_42_2 e_1_2_6_84_3 e_1_2_6_80_2 e_1_2_6_6_2 e_1_2_6_23_2 e_1_2_6_69_2 e_1_2_6_2_2 e_1_2_6_65_2 e_1_2_6_88_2 e_1_2_6_27_2 e_1_2_6_46_2 e_1_2_6_51_2 e_1_2_6_97_2 e_1_2_6_74_2 e_1_2_6_93_2 e_1_2_6_70_2 e_1_2_6_59_2 e_1_2_6_32_3 e_1_2_6_32_2 e_1_2_6_17_2 e_1_2_6_55_2 e_1_2_6_36_2 e_1_2_6_78_2 e_1_2_6_62_2 e_1_2_6_85_2 e_1_2_6_20_2 e_1_2_6_81_2 e_1_2_6_7_2 e_1_2_6_3_2 e_1_2_6_24_2 e_1_2_6_47_2 e_1_2_6_28_2 e_1_2_6_43_2 e_1_2_6_66_2 e_1_2_6_89_2 e_1_2_6_52_2 e_1_2_6_75_2 e_1_2_6_94_2 e_1_2_6_52_3 e_1_2_6_71_2 e_1_2_6_90_2 e_1_2_6_18_2 e_1_2_6_10_2 e_1_2_6_33_2 e_1_2_6_14_2 e_1_2_6_37_2 e_1_2_6_56_2 e_1_2_6_79_2 e_1_2_6_63_2 e_1_2_6_86_2 e_1_2_6_40_2 e_1_2_6_82_2 e_1_2_6_8_2 Muñoz M. P. (e_1_2_6_13_2) 2003 e_1_2_6_8_3 e_1_2_6_29_2 e_1_2_6_4_2 e_1_2_6_48_2 e_1_2_6_21_2 e_1_2_6_44_2 e_1_2_6_25_2 Hu, XL (WOS:000188872700017) 2004; 23 Chatani, N (WOS:000177881300023) 2002; 124 Mamane, V (WOS:000222704700032) 2004; 126 Marion, F (WOS:000221038000043) 2004; 6 NIETOOBERHUBER C (WOS:000235440200012.56) 2004; 116 Coxon, JM (WOS:000086348400039) 2000; 65 Chatani, N (WOS:000075860100040) 1998; 120 MATSUO, A (WOS:A1977DS73400007) 1977; 33 Méndez, M (WOS:000165600300049) 2000; 122 Bertani, R (WOS:A1997XK49700024) 1997; 16 Fraile, JM (WOS:000170299800018) 2001; 123 Nieto-Oberhuber, C (WOS:000232287700005) 2005; 44 Kaye, S (WOS:000173349900006) 2001; 343 Aubert, C (WOS:000174456500008) 2002; 102 TROST BM (WOS:000235440200012.76) 1993; 105 Bernardi, F (WOS:000169545500016) 2001; 20 NOZAKI, H (WOS:A1979GU80800026) 1979 Nieto-Oberhuber, C (WOS:000221307200013) 2004; 43 BROOKHART, M (WOS:A1987H740600001) 1987; 6 Diver, ST (WOS:000220153100006) 2004; 104 Fürstner, A (WOS:000172591000005) 2001; 123 CHATANI, N (WOS:A1994NV42100098) 1994; 116 Méndez, M (WOS:000171860700011) 2001; 123 Echavarren, AM (WOS:000223760400004) 2004; 33 HAY, PJ (WOS:A1985ABS5500035) 1985; 82 XU, DQ (WOS:A1994NH15300014) 1994; 35 Nevado, C (WOS:000183598400023) 2003; 9 de Frémont, P (WOS:000228945500020) 2005; 24 Echavarren, AM (WOS:000221367800002) 2004; 76 MAINETTI E (WOS:000235440200012.43) 2002; 114 Meyer, C (WOS:000186141300006) 2003; 36 Iwakura, I (WOS:000220207300023) 2004; 6 ANDERSEN, NH (WOS:A1978EJ34600004) 1978; 34 Lloyd-Jones, GC (WOS:000181557300001) 2003; 1 Bruneau, C (WOS:000228709200006) 2005; 44 Chatani, N (WOS:A1996TU70200003) 1996; 15 Singh, S (WOS:000231340900012) 2005 ANDERSEN, NH (WOS:A1977DY07800022) 1977; 16 Walker, SD (WOS:000220658400026) 2004; 43 Chauhan, AKS (WOS:000186209800007) 2003; 17 Mainetti, E (WOS:000176386900027) 2002; 41 Bajracharya, GB (WOS:000226777100017) 2005; 70 FRUCTOS MR (WOS:000235440200012.30) 2005; 117 Muñoz, MP (WOS:000227533800034) 2005; 24 Zhang, LM (WOS:000229085200025) 2005; 127 Nevado, C (WOS:000223581900044) 2004; 6 BOVIO, B (WOS:A1993LM42700042) 1993; 452 Kohn, W (WOS:A1996VA59500020) 1996; 100 FRISCH MJ (WOS:000235440200012.28) 1998 Trost, BM (WOS:000170369800015) 2001; 343 TROST, BM (WOS:A1991FY66700014) 1991; 32 Harrak, Y (WOS:000222704700033) 2004; 126 Straub, BF (WOS:000179404200047) 2002; 124 Nieto-Oberhuber, C (WOS:000228755300021) 2005; 127 STEPHENS, PJ (WOS:A1994PQ94400001) 1994; 98 TROST, BM (WOS:A1993LH97700050) 1993; 115 STRICKLER, H (WOS:A1976BT86100034) 1976; 59 BRUNEAU C (WOS:000235440200012.15) 2005; 117 Soriano, E (WOS:000229878200021) 2005; 24 TROST, BM (WOS:A1994NB16900084) 1994; 116 MATSUO, A (WOS:A1976CP94800006) 1976 Rodríguez-García, C (WOS:000169534000034) 2001; 123 TROST, BM (WOS:A1993LP90000038) 1993; 32 ALSAADY AK (WOS:000235440200012.1) 1985; 23 Schmitz, WD (WOS:000073136500003) 1998; 63 BLOMBERG, MRA (WOS:A1987J360000004) 1987; 109 BENESOVA, V (WOS:A1973P508900017) 1973; 38 NIETOOBERHUBER C (WOS:000235440200012.60) 2005; 117 Hayashi, K (WOS:000074422400011) 1998; 48 Fructos, MR (WOS:000231548200017) 2005; 44 BENESOVA, V (WOS:A1973O265000035) 1973; 12 Añorbe, L (WOS:000224600600001) 2004; 10 BENESOVA, V (WOS:A1971J682700024) 1971 SAUCY, G (WOS:A1967A144400044) 1967; 50 Shi, XD (WOS:000228602600037) 2005; 127 TROST, BM (WOS:A1988M369700054) 1988; 110 Luzung, MR (WOS:000223691300031) 2004; 126 Muñoz, MP (WOS:000187557700028) 2003 Strieter, ER (WOS:000186580600035) 2003; 125 Nevado, C (WOS:000180996100011) 2003; 2003 Zhang, LM (WOS:000224103900028) 2004; 126 |
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| SSID | ssj0009633 |
| Score | 2.2466505 |
| Snippet | Gold(I) complexes are the most active catalysts for the biscyclopropanation of dienynes to form tetracyclic compounds. PtII and ZnII are also able to promote... Gold( I ) complexes are the most active catalysts for the biscyclopropanation of dienynes to form tetracyclic compounds. Pt II and Zn II are also able to... Gold(I) complexes are the most active catalysts for the biscyclopropanation of dienynes to form tetracyclic compounds. Pt-II and Zn-II are also able to promote... |
| Source | Web of Science |
| SourceID | proquest pubmed webofscience crossref wiley istex |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 1694 |
| SubjectTerms | alkynes Chemistry Chemistry, Multidisciplinary cyclization density functional calculations gold Physical Sciences platinum Science & Technology zinc |
| Title | Gold(I)-Catalyzed Intramolecular Cyclopropanation of Dienynes |
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