A new ruthenium-catalyzed cyclopropanation of alkenes using propargylic acetates as a precursor of vinylcarbenoids

Tetrahedron Letters

Volumn 44, Issue 10, 2003, Pages 2019-2022

  Miki, Koji ^a   Ohe, Kouichi ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALKENE DERIVATIVE; CARBENOID; CARBON; CARBONYL DERIVATIVE; RUTHENIUM; VINYL DERIVATIVE;

ARTICLE; CATALYST; CYCLOPROPANATION; GAS LIQUID CHROMATOGRAPHY; MOLECULAR INTERACTION; PRECURSOR; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037416940     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00219-3     Document Type: Article

References (35)

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7. Transition metal-catalyzed reorganization reaction of enynes. For example, [Pd] cat.: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636; (b) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647; (c) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. [Ru] cat.: (d) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049. [Ru] or [Pt] cat.: (e) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9140; (f) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913. [Pt] cat.: (g) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901; (h) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704. [Ir] cat.: (i) Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433.
8. Transition metal-catalyzed reorganization reaction of enynes. For example, [Pd] cat.: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636; (b) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647; (c) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. [Ru] cat.: (d) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049. [Ru] or [Pt] cat.: (e) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9140; (f) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913. [Pt] cat.: (g) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901; (h) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704. [Ir] cat.: (i) Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433.
9. Transition metal-catalyzed reorganization reaction of enynes. For example, [Pd] cat.: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636; (b) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647; (c) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. [Ru] cat.: (d) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049. [Ru] or [Pt] cat.: (e) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9140; (f) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913. [Pt] cat.: (g) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901; (h) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704. [Ir] cat.: (i) Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433.
10. Transition metal-catalyzed reorganization reaction of enynes. For example, [Pd] cat.: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636; (b) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647; (c) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. [Ru] cat.: (d) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049. [Ru] or [Pt] cat.: (e) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9140; (f) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913. [Pt] cat.: (g) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901; (h) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704. [Ir] cat.: (i) Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433.
11. Transition metal-catalyzed reorganization reaction of enynes. For example, [Pd] cat.: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636; (b) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647; (c) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. [Ru] cat.: (d) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049. [Ru] or [Pt] cat.: (e) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9140; (f) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913. [Pt] cat.: (g) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901; (h) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704. [Ir] cat.: (i) Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433.
12. Transition metal-catalyzed reorganization reaction of enynes. For example, [Pd] cat.: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636; (b) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647; (c) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. [Ru] cat.: (d) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049. [Ru] or [Pt] cat.: (e) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9140; (f) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913. [Pt] cat.: (g) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901; (h) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704. [Ir] cat.: (i) Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433.
13. Transition metal-catalyzed reorganization reaction of enynes. For example, [Pd] cat.: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636; (b) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647; (c) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. [Ru] cat.: (d) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049. [Ru] or [Pt] cat.: (e) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9140; (f) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913. [Pt] cat.: (g) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901; (h) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704. [Ir] cat.: (i) Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433.
14. The reactions of α,ω-enynes with dienes via cyclopropylcarbene complexes have been reported. See: (a) Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085; (b) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. For the reactions of α,ω-enynes with alcohols via cyclopropylcarbene complexes, see: (c) Méndez, M.; Muñoz, M. P.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 11549; (d) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511.
15. The reactions of α,ω-enynes with dienes via cyclopropylcarbene complexes have been reported. See: (a) Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085; (b) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. For the reactions of α,ω-enynes with alcohols via cyclopropylcarbene complexes, see: (c) Méndez, M.; Muñoz, M. P.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 11549; (d) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511.
16. The reactions of α,ω-enynes with dienes via cyclopropylcarbene complexes have been reported. See: (a) Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085; (b) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. For the reactions of α,ω-enynes with alcohols via cyclopropylcarbene complexes, see: (c) Méndez, M.; Muñoz, M. P.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 11549; (d) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511.
17. The reactions of α,ω-enynes with dienes via cyclopropylcarbene complexes have been reported. See: (a) Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085; (b) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. For the reactions of α,ω-enynes with alcohols via cyclopropylcarbene complexes, see: (c) Méndez, M.; Muñoz, M. P.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 11549; (d) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511.
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24. Transition metal-catalyzed isomerization of propargylic acetates has been established as a standard method to prepare allenyl acetates. See: (a) Schlossarczyk, H.; Sieber, W.; Hesse, M.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1973, 56, 875; (b) Oelberg, D. G.; Schiavelli, M. D. J. Org. Chem. 1977, 42, 1804; (c) Cookson, R. C.; Cramp, M. C.; Parsons, P. J. J. Chem. Soc., Chem. Commun. 1980, 197 and references cited therein.
25. Transition metal-catalyzed isomerization of propargylic acetates has been established as a standard method to prepare allenyl acetates. See: (a) Schlossarczyk, H.; Sieber, W.; Hesse, M.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1973, 56, 875; (b) Oelberg, D. G.; Schiavelli, M. D. J. Org. Chem. 1977, 42, 1804; (c) Cookson, R. C.; Cramp, M. C.; Parsons, P. J. J. Chem. Soc., Chem. Commun. 1980, 197 and references cited therein.
26. Transition metal-catalyzed isomerization of propargylic acetates has been established as a standard method to prepare allenyl acetates. See: (a) Schlossarczyk, H.; Sieber, W.; Hesse, M.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1973, 56, 875; (b) Oelberg, D. G.; Schiavelli, M. D. J. Org. Chem. 1977, 42, 1804; (c) Cookson, R. C.; Cramp, M. C.; Parsons, P. J. J. Chem. Soc., Chem. Commun. 1980, 197 and references cited therein.
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31. 2: C, 78.23; H, 7.88. Found: C, 77.96; H, 7.91%.
32. Recently, Yamamoto et al. have reported indenol ether formation from aryl alkynes via Pd-carbene intermediates. See: Nakamura I., Bajracharya G.B., Mizushima Y., Yamamoto Y. Angew. Chem., Int. Ed. 41:2002;4328.
33. Geometry of alkenic part is temporarily assigned to Z due to no appreciable NOE between a vinylic proton and methyl protons of an acetyl group.
34. 6 catalyst. See: (a) Kikuchi, H.; Uno, M.; Takahashi, S. Chem. Lett. 1997, 1273; (b) Matsushima, Y.; Kikuchi, H.; Uno, M.; Takahashi, S. Bull. Chem. Soc. Jpn. 1999, 72, 2475.
35. 6 catalyst. See: (a) Kikuchi, H.; Uno, M.; Takahashi, S. Chem. Lett. 1997, 1273; (b) Matsushima, Y.; Kikuchi, H.; Uno, M.; Takahashi, S. Bull. Chem. Soc. Jpn. 1999, 72, 2475.