Nai-Xing Wang and Jia Zhao
COMMUNICATIONS
left to stir overnight at room temperature, during the time a
yellow precipitate formed. The product was collected by fil-
tration and purified by gel chromatography (Sephadex LH-
20, CH3OH) to give 1 as a yellow solid; yield: 0.16 g (yield
42%); 1H NMR [400 MHz, (CD3)2SO]: d=1.20 (m, 12H,
CH2CH2CHNH), 1.52–1.54 (m, 6H, CH2CHH’CHNH), 1.78
(m, 6H, CH2CHH’CHNH), 2.64 (d, J=18.3 Hz, 3H, pyr-4-
CHH’), 3.03 (d, J=18.3 Hz, 3H; pyr-4-CHH’), 3.63 (m, 3H,
CHNH), 3.78–3.80 (m, 3H, CHNH), 3.95 (d, J=14.1 Hz,
3H, ArCHH’), 4.56 (d, J=14.1, 3H, ArCHH’), 6.44 (s, 3H,
C6H3), 6.92 (d, J=8.4 Hz, 3H, CHNH), 7.06 (d, J=7.6 Hz,
3H, CHNH), 7.16 (s, 3H, pyr-2,6-CHCH’), 7.21 (s, 3H, pyr-
2,6-CHCH’); 13C NMR [150 MHz, (CD3)2SO]: d=25.2
7036–7040; b) P. M. T. De Kok, L. A. M. Bastiaansen,
P. M. Van Lier, J. A. J. M. Vekemans, H. M. Buck, J.
Org. Chem. 1989, 54, 1313–1320; c) X. Li, D. D.
Tanner, Tetrahedron Lett. 1996, 37, 3275–3278.
[4] a) J. G. De Vries, R. M. Kellogg, J. Am. Chem. Soc.
1979, 101, 2759–2761; b) P. Jouin, C. B. Troostwijk,
R. M. Kellogg, J. Am. Chem. Soc. 1981, 103, 2091–
2093; c) M. Seki, N. Baba, J. Oda, Y. Inouye, J. Am.
Chem. Soc. 1981, 103, 4613–4615; d) K. Skog, O. Wen-
nerstrçm, Tetrahedron Lett. 1992, 33, 1751–1754; K.
Skog, O. Wennerstrçm, Tetrahedron Lett. 1995, 36,
4629–4632; e) Y. Kuroda, H. Seshimo, T. Kondo, M.
Shiba, H. Ogoshi, Tetrahedron Lett. 1997, 38, 3939–
3942; f) U. Gran, O. Wennerstrçm, G. Westman, Tetra-
hedron 2001, 57, 8897–8902; g) U. Gran, Tetrahedron
2003, 59, 4303–4308; h) U. Gran, O. Wennerstrçm, G.
Westman, Tetrahedron: Asymmetry 2000, 11, 3027–
3040.
(CH2CH2CHNH),
25.6
(C’H2CH2CHNH),
32.0
(CH2CHNH), 32.9 (C’H2CHNH), 40.5 (pyr-4-CH2), 52.0
(CHNH), 53.0 (C’HNH), 57.3 (ArCH2), 107.3 (pyr-3,5-CC’),
109.1 (pyr-3,5-CC’), 127.7 (Ar-2,4,6-CH), 132.6 (Ar-1,3,5-C),
136.2 (pyr-2,6-CHC’H), 138.1 (pyr-2,6-CHC’H), 167.0, 167.1
(C=O); ESI-MS: m/z=856.7 [M+H]+, 873.8 [M+Na]+; HR-
MS (ESI): m/z=854.43633, calcd. for [MÀH]: 854.43590;
[a]D: À238.28 (c 0.002, DMSO).
[5] a) W. P. Cochrane, P. L. Pauson, T. S. Stevens, J. Chem.
Soc. C 1968, 630–632; b) Y. Yamagiwa, Y. Koreishi, S.
Kiyozumi, M. Kobayashi, T. Kamikawa, M. Tsukino, H.
Goi, M. Yamamoto, M. Munakata, Bull. Chem. Soc.
Jpn. 1996, 69, 3317–3323.
[6] K. J. Wallace, W. J. Belcher, D. R. Turner, K. F. Syed,
W. J. Steed, J. Am. Chem. Soc. 2003, 125, 9699–9715.
[7] a) A. L. J. Beckwith, S. W. Westwood, Tetrahedron
1989, 45, 5269–5282; b) Y.-S. Wong, C. Marazano, D.
Gnecco, B. C. Das, Tetrahedron Lett. 1994, 35, 707–710.
[8] J. F. Larrow, E. N. Jacobson, Y. Gao, Y.-P. Hong, X.-Y.
Nie, C. M. Zepp, J. Org. Chem. 1994, 59, 1939–1942.
[9] a) W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029–
3070; b) C. Jaekel, R. Paciello, Chem. Rev. 2006, 106,
2912–2942.
[10] a) J. Guin, R. Frçhlich, A. Studer, Angew. Chem. 2008,
120, 791–794; Angew. Chem. Int. Ed. 2008, 47, 779–
782; b) Q. Kang, Z.-A. Zhao, S.-L. You, Adv. Synth.
Catal. 2007, 349, 1657–1660.
[11] a) G. Ouellet, A. M. Walji, D. W. C. Macmillan, Acc.
Chem. Res. 2007, 40, 1327–1339; b) S. J. Connon, Org.
Biomol. Chem. 2007, 5, 3407–3417; c) J. W. Yang, B.
List, Org. Lett. 2006, 8, 5653–5655; d) S. L. You, Chem.
Asian J. 2007, 2, 820–827.
[12] G. Li, J. C. Antilla, Org. Lett. 2009, 11, 1075–1078.
[13] L. Simꢃn, J. M. Goodman, J. Am. Chem. Soc. 2008,
130, 8741–8747.
[14] a) F. W. D. Rost, Fluorescence Microscopy, Vol II, Cam-
bridge University Press, New York, 1995; b) C. H.
Blomquist, J. Biol. Chem. 1969, 244, 1605–1607.
[15] a) S. H. Ihm, J. O. Lee, S. J. Kim, K. B. Seung, V. B.
Schini-Kerth, K. Chang, M. H. Oak, Atherosclerosis
2009, 206, 45–53; b) V. Sashuk, D. Schoeps, H. Plenio,
Chem. Commun. 2009, 770–772.
Acknowledgements
Support for this research was provided by the Natural Science
Foundation of China (20472090 and 10576034).
References
[1] a) U. Eisner, J. Kuthan, Chem. Rev. 1972, 72, 1–42;
b) D. M. Stout, A. I. Meyers, Chem. Rev. 1982, 82, 223–
243; c) V. A. Burgess, S. G. Davies, R. T. Skerlj, Tetra-
hedron: Asymmetry 1991, 2, 299–328; d) Y. Murakami,
J.-i. Kikuchi, Y. Hisaeda, O. Hayashida, Chem. Rev.
1996, 96, 721–758; e) N. X. Wang, J. Zhao, Synlett
2007, 18, 2785–2791; f) N. Kanomata, T. Nakata, J.
Am. Chem. Soc. 2000, 122, 4563–4568.
[2] a) V. A. Burgess, S. G. Davies, R. T. Skerlj, J. Chem.
Soc. Chem. Commun. 1990, 1759–1762; b) Y. Combret,
J. J. Torchꢂ, B. Binay, G. Dupas, J. Bourguignon, G.
Quꢂguiner, Chem. Lett. 1991, 20, 125–128; c) Y. Com-
bret, J. Duflos, G. Dupas, J. Bourguignon, G. Quꢂguin-
er, Tetrahedron: Asymmetry 1993, 4, 1635–1644; Y.
Combret, J. Duflos, G. Dupas, J. Bourguignon, G. Quꢂ-
guiner, Tetrahedron 1993, 49, 5237–5246; d) J. Bꢂdat,
V. Levacher, G. Dupas, G. Quꢂguiner, J. Bourguignon,
Chem. Lett. 1996, 25, 359–360.
[3] a) A. Ohno, M. Ikeguchi, T. Kimura, S. Oka, J. Chem.
Soc. Chem. Commun. 1978, 328–329; A. Ohno, M. Ike-
guchi, T. Kimura, S. Oka, J. Am. Chem. Soc. 1979, 101,
3050
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Adv. Synth. Catal. 2009, 351, 3045 – 3050