A novel modified Baylis-Hillman reaction of propiolate

Journal of the American Chemical Society

Volumn 125, Issue 3, 2003, Pages 646-647

  Matsuya, Yuji ^a   Hayashi, Kousuke ^a   Nemoto, Hideo ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL STRUCTURE; COMPLEX FORMATION; DIMERIZATION; MOLECULAR DYNAMICS; REACTION ANALYSIS;

EID: 0037460191     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028312k     Document Type: Article

References (48)

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31. The geometry was determined by an NOE experiment between the olefinic proton and the methyne proton bearing a trimethylsilyloxy group.
32. Highly electron-deficient aldehydes such as 4-nitro or pentafluorobenzaldehyde afforded a complex mixture under the reaction conditions.
33. According to this mechanism, DABCO should act in a catalytic fashion. Using 10 mol % of DABCO, however, the product yield decreased considerably, although the yield % was over the amount of DABCO.
34. Recently, it was reported that the reaction of aromatic aldehydes, DMAD, and catalytic pyridine gave 2-oxo-3-benzylidenesuccinates via oxetene intermediate. However, in our reaction, the product based on this mechanism could not be detected, probably due to predominance of silyl migration over the formation of strained oxetene ring. See; Nair, V.; Sreekanth, A. R.; Vinod, A. U. Org. Lett. 2001, 3, 3495.
35. Reviews on nature and reactivity of alkylidene carbene: (a) Stang, P. J. Acc. Chem. Res. 1982, 15, 348. (b) Stang, P. J. Chem. Rev. 1978, 78, 383.
36. Reviews on nature and reactivity of alkylidene carbene: (a) Stang, P. J. Acc. Chem. Res. 1982, 15, 348. (b) Stang, P. J. Chem. Rev. 1978, 78, 383.
37. Recent reports on generation of alkylidene carbene and their applications: (a) Chernick, E. T.; Eisler, S.; Tykwinski, R. R. Tetrahedron Lett. 2001, 42, 8575. (b) Feldman, K. S.; Perkins, A. L. Tetrahedron Lett. 2001, 42, 6031. (c) Tobe, Y.; Iwasa, N.; Umeda, R.; Sonoda, M. Tetrahedron Lett. 2001, 42, 5485. (d) Ohira, S.; Yamasaki, K.; Nozaki, H.; Yamato, M.; Nakayama, M. Tetrahedron Lett. 1995, 36, 8843. (e) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (f) Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135.
38. Recent reports on generation of alkylidene carbene and their applications: (a) Chernick, E. T.; Eisler, S.; Tykwinski, R. R. Tetrahedron Lett. 2001, 42, 8575. (b) Feldman, K. S.; Perkins, A. L. Tetrahedron Lett. 2001, 42, 6031. (c) Tobe, Y.; Iwasa, N.; Umeda, R.; Sonoda, M. Tetrahedron Lett. 2001, 42, 5485. (d) Ohira, S.; Yamasaki, K.; Nozaki, H.; Yamato, M.; Nakayama, M. Tetrahedron Lett. 1995, 36, 8843. (e) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (f) Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135.
39. Recent reports on generation of alkylidene carbene and their applications: (a) Chernick, E. T.; Eisler, S.; Tykwinski, R. R. Tetrahedron Lett. 2001, 42, 8575. (b) Feldman, K. S.; Perkins, A. L. Tetrahedron Lett. 2001, 42, 6031. (c) Tobe, Y.; Iwasa, N.; Umeda, R.; Sonoda, M. Tetrahedron Lett. 2001, 42, 5485. (d) Ohira, S.; Yamasaki, K.; Nozaki, H.; Yamato, M.; Nakayama, M. Tetrahedron Lett. 1995, 36, 8843. (e) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (f) Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135.
40. Recent reports on generation of alkylidene carbene and their applications: (a) Chernick, E. T.; Eisler, S.; Tykwinski, R. R. Tetrahedron Lett. 2001, 42, 8575. (b) Feldman, K. S.; Perkins, A. L. Tetrahedron Lett. 2001, 42, 6031. (c) Tobe, Y.; Iwasa, N.; Umeda, R.; Sonoda, M. Tetrahedron Lett. 2001, 42, 5485. (d) Ohira, S.; Yamasaki, K.; Nozaki, H.; Yamato, M.; Nakayama, M. Tetrahedron Lett. 1995, 36, 8843. (e) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (f) Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135.
41. Recent reports on generation of alkylidene carbene and their applications: (a) Chernick, E. T.; Eisler, S.; Tykwinski, R. R. Tetrahedron Lett. 2001, 42, 8575. (b) Feldman, K. S.; Perkins, A. L. Tetrahedron Lett. 2001, 42, 6031. (c) Tobe, Y.; Iwasa, N.; Umeda, R.; Sonoda, M. Tetrahedron Lett. 2001, 42, 5485. (d) Ohira, S.; Yamasaki, K.; Nozaki, H.; Yamato, M.; Nakayama, M. Tetrahedron Lett. 1995, 36, 8843. (e) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (f) Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135.
42. Recent reports on generation of alkylidene carbene and their applications: (a) Chernick, E. T.; Eisler, S.; Tykwinski, R. R. Tetrahedron Lett. 2001, 42, 8575. (b) Feldman, K. S.; Perkins, A. L. Tetrahedron Lett. 2001, 42, 6031. (c) Tobe, Y.; Iwasa, N.; Umeda, R.; Sonoda, M. Tetrahedron Lett. 2001, 42, 5485. (d) Ohira, S.; Yamasaki, K.; Nozaki, H.; Yamato, M.; Nakayama, M. Tetrahedron Lett. 1995, 36, 8843. (e) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (f) Ochiai, M.; Kunishima, M.; Tani, S.; Nagao, Y. J. Am. Chem. Soc. 1991, 113, 3135.
43. This compound was synthesized by treatment of methyl propiolate with LDA followed by benzaldehyde and trimethylsilyl chloride, successively.
44. For the reaction of carbene with aldehydes; (a) de March, P.; Huisgen, R. J. Am. Chem. Soc. 1982, 104, 4952. (b) L'Esperance, R. P.; Ford, T. M.; Jones, M., Jr. J. Am. Chem. Soc. 1988, 110, 209. In these reports, formation of oxirane or dioxorane via carbonyl ylide is described. Thus, the reaction described here is the first example of direct C-H insertion of aldehyde into a carbene to our best knowledge.
45. For the reaction of carbene with aldehydes; (a) de March, P.; Huisgen, R. J. Am. Chem. Soc. 1982, 104, 4952. (b) L'Esperance, R. P.; Ford, T. M.; Jones, M., Jr. J. Am. Chem. Soc. 1988, 110, 209. In these reports, formation of oxirane or dioxorane via carbonyl ylide is described. Thus, the reaction described here is the first example of direct C-H insertion of aldehyde into a carbene to our best knowledge.
46. Although it seems that the stereochemistry of the product 2 is regulated in this last step, it remains unclear what caused the exclusive selectivity. As another possibility, the selectivity might be controlled thermodynamically via E-Z isomerization, not kinetically.
47. In a recent report on the acylation of vinylselenonium ylide with aldehydes, it is described that benz(aldehyde-d) did not give the deuterated product. This implies that the mechanism of our reaction is different from that proposed in the literature, which includes allenoate intermediate, not via alkylidene carbene. See; Watanabe, S.; Kusumoto, T.; Yoshida, C.; Kataoka, T. Chem. Commun. 2001, 839.
48. For experimental detaild and spectral data, see Supporting Information.