Rhodium-catalyzed carbene-transfer reactions via thienylcarbene complexes generated from thiocarbamoyl-ene-yne compounds

Synlett

Volumn , Issue 5, 2011, Pages 655-658

  Tsuneishi, Asuka ^a   Okamoto, Kazuhiro ^a   Ikeda, Yuji ^a   Murai, Masahito ^a   Miki, Koji ^a   Ohe, Kouichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

carbene complex; cyclopropanation; rhodium; ring opening reaction; thiocarbamoyl ene yne

Indexed keywords

CARBENE; FURAN DERIVATIVE; RHODIUM; THIENYLCARBENE COMPLEX; THIOCARBAMOYL ENE YNE COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOPROPANATION; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; ROOM TEMPERATURE; SYNTHESIS;

EID: 79952441009     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259559     Document Type: Article

References (22)

1. Zaragozasm Dörward F, Metal Carbenes in Organic Synthesis Wiley-VCH Weinheim 1999
2. Metal Carbenes in Organic Synthesis, In Topics in Organometallic Chemistry Vol. 13 Dötz K H. Springer Berlin 2004
3. Doyle M P., McKervey M A., Ye T, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds Wiley-Interscience New York 1998
4. Miki K, Uemura S, Ohe K, Chem. Lett. 2005 34 1068
5. Kusama H, Iwasawa N, Chem. Lett. 2006 35 1082
6. Ohe K, Bull. Korean Chem. Soc. 2007 28 2153
7. Ohe K, Miki K, J. Synth. Org. Chem. Jpn. 2009 67 1161
8. Miki K, Nishino F, Ohe K, Uemura S, J. Am. Chem. Soc. 2002 124 5260
9. Nishino F, Miki K, Kato Y, Ohe K, Uemura S, Org. Lett. 2003 5 2615
10. Miki K, Yokoi T, Nishino F, Kato Y, Washitake Y, Ohe K, Uemura S, J. Org. Chem. 2004 69 1557
11. Thiocarbamoyl moiety was also used for the generation of vinylcarbene complexes. See:, Ikeda Y, Murai M, Abo T, Miki K, Ohe K, Tetrahedron Lett. 2007 48 6651
12. Thiocarbamoyl-ene-yne 1 was synthesized in two steps from 1,2-dibromocyclohexene, which was prepared according to the known procedure. See:, Voigt K, von Zezschwitz P, Rosauer K, Lansky A, Adams A, Reiser O, de Meijere A, Eur. J. Org. Chem. 1998 1521
13. In sharp contrast, the reaction of carbamoyl-ene-yne compounds with a chromium complex gives not furyl carbene-chromium complexes but pyranylidene-chromium complexes. Theoretical investigations are in progress and will be published in due course. See:, Ohe K, Miki K, Yokoi T, Nishino F, Uemura S, Organometallics 2000 19 5525
14. Miki K, Yokoi T, Nishino F, Ohe K, Uemura S, J. Organomet. Chem. 2002 645 228
15. Pirrung M C., Zhang J, Lackey K, Strenbach D D., Brown F, J. Org. Chem. 1995 60 2112
16. Shieh C P., Ong C W., Tetrahedron 2001 57 7303
17. Miki K, Fujita M, Kato Y, Uemura S, Ohe K, Org. Lett. 2006 8 1741
18. Katritzky A R., Ramsden C A., Joule J A., Zhdankin V V., Handbook of Heterocyclic Chemistry 3rd ed. Elsevier Amsterdam 2010 126-128
19. Rhodium-catalyzed ring-opening reaction of 2-methoxy-thiophene with ethyl diazoacetate has been reported. See:, Tranmer G K., Capreta A, Tetrahedron 1998 54 15499
20. 2-Aminothiophenes were synthesized according reported procedures. See:, Lu Z, Twieg R J., Tetrahedron 2005 61 903
21. Gillespie R J., Porter A E. A., J. Chem. Soc., Perkin Trans. 1 1979 2624
22. Lee Y R., Cho B S., Bull. Korean Chem. Soc. 2002 23 779