A Straightforward Procedure for the [2+2+2]Cycloaddition of Enediynes
UPDATES
L.-P. Li, D.-J. Huang, C.-L. Lin, D. K. Rayabarapu, C.-
H. Cheng, J. Org. Chem. 1999, 64, 3663; n) N. Mori, S.
Ikeda, Y. Sato, J. Am. Chem. Soc. 1999, 121, 2722; o) S.
Ikeda, H. Kondo, T. Arii, K. Odashima, Chem.
Commun. 2002, 2422; p) T. N. Tekevac, J. Louie Org.
Lett. 2005, 7, 4037 and references cited therein.
[10] So far, rhodium catalysts remain the best choice for
achieving enantioselective [2+2+2]cycloadditions, see
refs.[9d–f] and a) K. Tanaka, Synlett 2007, 1977; in partic-
ular, for enantioselective preparations of 1,3-cyclohexa-
dienes, see refs.[9d,i,h] and b) P. Evans, A. K. W. Lai, J. R.
Sawyer, J. Am. Chem. Soc. 2005, 127, 12466; c) K. Tsu-
chikama, Y. Kuwata, T. Shibata, J. Am. Chem. Soc.
2006, 128, 13686; d) T. Shibata, H. Kurokawa, K.
Kanda, J. Org. Chem. 2007, 72, 6521.
[11] a) F. Slowinski, C. Aubert, M. Malacria, Adv. Synth.
Catal. 2001, 343, 64; b) M.-S. Wu, M. Shanmugasundar-
am, C.-H. Cheng, Chem. Commun. 2003, 718; c) M.-S.
Wu, D. K. Rayabarapu, C.-H. Cheng, Tetrahedron 2004,
60, 10005; d) G. Hilt, T. Vogler, W. Hess, F. Galbiati,
Chem. Commun. 2005, 1474; e) N. Saino, F. Amemiya,
E. Tanabe, K. Kase, S. Okamoto, Org. Lett. 2006, 8,
1439; f) L. Doszczak, P. Fey, R. Tacke, Synlett 2007,
753; g) M. W. Bꢇttner, J. B. Nꢈtscher, C. Burschka, R.
Tacke, Organometallics 2007, 26, 4835; h) L. Doszczak,
R. Tacke, Organometallics 2007, 26, 5722; i) G. Hilt, W.
Hess, K. Harms, Synthesis 2008, 75; j) G. Hilt, A. Paul,
K. Harms, J. Org. Chem. 2008, 73, 5187.
[12] K. Kase, A. Goswami, K. Ohtaki, E. Tanabe, N. Saino,
S. Okamoto, Org. Lett. 2007, 9, 931; see also: H. Bçn-
nemann, R. Brinkmann, H. Schenkluiin, Synthesis 1974,
575.
[13] a) G. P. Chiusoli, M. Costa, S. Reverberi, M. G. Teren-
ghi, Transition Met. Chem. 1989, 14, 238; b) G. P. Chiu-
soli, L. Pallini, G. Terenghi, Transition Met. Chem.
1984, 9, 360.
[14] a) G. Hilt, S. Lꢇers, K. Harms, J. Org. Chem. 2004, 69,
624; b) G. Hilt, F. Galbiati, Synlett 2005, 829; c) G. Hilt,
W. Hess, K. Harms, Org. Lett. 2006, 8, 3287; d) G. Hilt,
W. Hess, T. Vogler, C. Hengst, J. Organomet. Chem.
2005, 690, 5170; e) G. Hilt, J. Janikowski, W. Hess,
Angew. Chem. 2006, 118, 5328; Angew. Chem. Int. Ed.
2006, 45, 5204.
[15] a) O. Pardigon, A. Tenaglia, G. Buono, J. Org. Chem.
1995, 60, 1868; b) I-F. Duan, C.-H. Cheng, J.-S. Shaw,
S.-S. Cheng, K. F. Liou, J. Chem. Soc. Chem. Commun.
1991, 1347; c) M. Lautens, W. Tam, J. Craig Lautens,
L. G. Edwards, C. M. Crudden, A. C. Smith, J. Am.
Chem. Soc. 1995, 117, 6863; d) J. E. Lyons, H. K.
Myers, A. Schneider, J. Chem. Soc., Chem. Commun.
1978, 636.
[19] G. Hilt, J. Janikowski, Angew. Chem. 2008, 120, 5321;
Angew. Chem. Int. Ed. 2008, 47, 5243.
[20] H.-T. Chang, M. Jeganmohan, C.-H. Cheng, Chem. Eur.
J. 2007, 13, 4356.
[21] Y.-C. Wong, T. T. Jayanth, C.-H. Cheng, Org. Lett.
2006, 8, 5613.
[22] M. Lombardo, A. Gualandi, F. Pasi, C. Trombini, Adv.
Synth. Catal. 2007, 349, 465.
[23] a) M. Amatore, C. Gosmini, J. Pꢂrichon, Eur. J. Org.
Chem. 2005, 989; b) M. Amatore, C. Gosmini, J. Pꢂri-
chon, J. Org. Chem. 2006, 71, 6130; c) M. Amatore, C.
Gosmini, Angew. Chem. 2008, 120, 2119; Angew.
Chem. Int. Ed. 2008, 47, 2089.
[24] The metal might be trapped as an unreactive h4-cyclo-
hexadiene complex (see Introduction), unstable over
SiO2, but we could not ascertain this possibility.
[25] Heteroannular 1,3-dienes are thermodynamically more
stable than homoannular ones, see inter alia: a) L.
Dorfman, Chem. Rev. 1953, 53, 47; b) R. P. Narasinha,
H. R. Gollberg, Tetrahedron 1962, 18, 1251; c) L. R.
Hanton, S. D. Lorimer, R. T. Weavers Aust. J. Chem.
1987, 40, 1795.
[26] For reviews on NHC, see inter alia: a) N-Heterocyclic
Carbenes, in: Transition Metal Catalysis, in: Topics in
Organometallic Chemistry, (Ed.: F. Glorius), Springer,
Heidelberg, 2007, Vol. 21; b) N-Heterocyclic Carbenes
in Synthesis, (Ed.: S. P. Nolan), Wiley-VCH, Weinheim,
2006; c) R. H. Crabtree, J. Organomet. Chem. 2005,
690, 5451; d) W. A. Herrmann, Angew. Chem. 2002,
114, 1342; Angew. Chem. Int. Ed. 2002, 41, 1290; e) D.
Bourissou, O. Guerret, F. P. Gabbaꢀ, G. Bertrand,
Chem. Rev. 2000, 100, 39; f) R. H. Crabtree, J. Organo-
met. Chem. 2005, 690, 5451; g) E. A. B. Kantchev, C. J.
OꢉBrien, M. G. Organ, Angew. Chem. 2007, 119, 2824;
Angew. Chem. Int. Ed. 2007, 46, 2768.
[27] For selected examples, see: a) S. A. Llewellyn, M. L. H.
Green, A. R. Cowley, Dalton Trans. 2006, 4164; b) H.
van Rensburg, R. P. Tooze, D. F. Foster, A. M. Z.
Slawin, Inorg. Chem. 2004, 43, 2468; c) X. Hu, K.
Meyer, J. Organomet. Chem. 2005, 690, 5474; d) A. A.
Danopoulos, J. A. Wright, W. B. Motherwell, S. Ell-
wood, Organometallics 2004, 23, 4807; e) A. M. Poul-
ton, S. D. R. Christie, R. Fryatt, S. H. Dale, M. R. J.
Elsegood, D. M. Andrews, Synlett 2004, 2103; f) E.
Fooladi, B. Dalhus, M. Tilset, Dalton Trans. 2004, 3909.
[28] N. Saino, D. Kogure, S. Okamoto, Org. Lett. 2005, 7,
3065.
[29] H. Someya, H. Ohmiya, H. Yorimitsu, K. Oshima, Org.
Lett. 2007, 9, 1565.
[30] T. Kobayashi, H. Ohmiya, H. Yorimitsu, K. Oshima, J.
Am. Chem. Soc. 2008, 130, 11276.
[31] See inter alia ref.[4c].
[16] G. Hilt, J. Treutwein, Angew. Chem. 2007, 119, 8653;
Angew. Chem. Int. Ed. 2007, 46, 8500.
[32] The carbene is now also commercially available and
can be used directly.
[17] a) M. Achard, A. Tenaglia, G. Buono, Org. Lett. 2005,
7, 2353; b) M. Achard, M. Mosrin, A. Tenaglia, G.
Buono, J. Org. Chem. 2006, 71, 2907.
[33] We checked that CoI2/Mn/imidazolium chloride, CoI2/
Mn/BuLi, CoI2/NHC, or even the NHC alone did ac-
tually not catalyze the cyclization.
[18] H.-T. Chang, T. T. Jayanth, C.-H. Cheng J. Am. Chem.
[34] This is of course critically dependent on the quality of
Mn.
Soc. 2007, 129, 4166.
Adv. Synth. Catal. 2009, 351, 271 – 275
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