Selenium-Containing Bicyclic β-Lactams through Enyne Metathesis
836 cm–1. MS (EI): m/z = 344 [M – tBu]+. HRMS: calcd. for
C14H22NO2SeSi 344.0585; found 400.0570.
[2] a) B. Alcaide, P. Almendros, P. C. Aragoncillo, Chem. Rev.
2007, 107, 4437–4492; b) I. Ojima, Acc. Chem. Res. 1995, 28,
383–389; c) A. J. Walz, M. J. Miller, Tetrahedron Lett. 2007, 48,
5103–5105.
[3] a) M. W. Carland, R. L. Martin, C. H. Schiesser, Org. Biomol.
Chem. 2004, 2, 2612–2618; b) M. W. Carland, C. H. Schiesser,
Molecules 2004, 9, 466; c) G. A. Brown, K. M. Anderson, J. M.
Large, D. Planchenault, D. Urban, N. J. Hales, T. Gallagher, J.
Chem. Soc. Perkin Trans. 1 2001, 1897–1900; d) M. W. Carland,
R. L. Martin, C. H. Schiesser, Tetrahedron Lett. 2001, 42,
4737–4739; e) G. A. Brown, K. M. Anderson, M. Murray, T.
Gallagher, N. J. Hales, Tetrahedron 2000, 56, 5579–5586; f) M.
Alpegiani, A. Bedeschi, E. Perrone, G. Franceschi, Tetrahedron
Lett. 1986, 27, 3041–3414.
(7R,8S)-4-(But-1-en-2-yl)-8-[(R)-1-(tert-butyldimethylsilyloxy)-
ethyl]-1-aza-6-selenabicyclo[5.2.0]dec-3-en-9-one (10c): Yield 9.5 mg
1
(46%). H NMR (CDCl3): δ = 0.06 (s, 3 H), 0.07 (s, 3 H), 0.86 (s,
9 H), 1.07 (t, J = 7.6 Hz, 3 H), 1.20 (d, J = 6.2 Hz, 3 H), 2.24–2.30
(q, J = 7.6 Hz, 2 H), 3.15 (dd, J = 1.4, 3.5 Hz, 1 H), 3.44 (d, J =
13.1 Hz, 1 H), 3.65 (d, J = 13.1 Hz, 1 H), 3.84 (dd, J = 6.1, 15.9 Hz,
1 H), 4.19–4.24 (m, 1 H), 4.30 (dd, J = 6.1, 15.9 Hz, 1 H), 5.02 (s,
2
77Se,1H
1 H), 5.07 (d, J = 1.4, J
= 19.2 Hz, 1 H), 5.11 (s, 1 H), 5.68
(t, J = 6.2 Hz, 1 H) ppm. 13C NMR (CDCl3): δ = –5.15, –4.22,
13.0, 17.8, 19.3, 22.6, 25.7, 26.5, 39.6, 48.8, 64.7, 68.1, 111.1, 118.1,
145.8, 148.6, 165.4 ppm. 77Se NMR (CDCl3): δ = 347.1 ppm. IR
[4] D. R. Garud, H. Ando, Y. Kawai, H. Ishihara, M. Koketsu,
Org. Lett. 2007, 9, 4455–4458.
(CHCl ): ν = 2955, 1760, 1630, 1462, 1385, 1253, 1065, 835 cm–1.
˜
3
MS (EI): m/z = 358 [M – tBu]+. HRMS: calcd. for C15H24NO2SeSi
[5] D. R. Garud, M. Koketsu, Org. Lett. 2008, 10, 3319–3322.
[6] For selected publications see: a) C. A. Tarling, A. B. Holmes,
R. E. Markwell, N. D. Pearson, J. Chem. Soc. Perkin Trans.
1 1999, 1695–1702; b) A. G. M. Barrett, S. P. D. Baugh, V. C.
Gibson, M. R. Giles, E. L. Marshall, P. A. Procopiou, Chem.
Commun. 1996, 2231–2232; c) A. G. M. Barrett, S. P. D. Baugh,
V. C. Gibson, M. R. Giles, E. L. Marshall, P. A. Procopiou,
Chem. Commun. 1997, 155–156; d) A. G. M. Barrett, S. P. D.
Baugh, D. C. Braddock, K. Flack, V. C. Gibson, M. R. Giles,
E. L. Marshall, P. A. Procopiou, A. J. P. White, D. J. Williams,
J. Org. Chem. 1998, 63, 7893–7907; e) A. G. M. Barrett, M.
Ahmed, S. P. Baker, S. P. D. Baugh, D. C. Braddock, P. A. Pro-
copiou, A. J. P. White, D. J. Williams, J. Org. Chem. 2000, 65,
3716–3721; f) S. Karsch, D. Freitag, P. Schwab, P. Metz, Syn-
thesis 2004, 1696–1712; g) D. Freitag, P. Schwab, P. Metz, Tet-
rahedron Lett. 2004, 45, 3589–3592; h) N. Desroy, F. Robert-
Peillard, J. Toueg, R. Duboc, C. Hénaut, M.-N. Rager, M. Savi-
nac, J.-P. Genêt, Eur. J. Org. Chem. 2004, 4840–4849.
[7] For selected review papers see: a) V. Michelet, P. Y. Toullec, J.-
P. G e n êt, Angew. Chem. Int. Ed. 2008, 47, 4268–4315; b) H.
Villar, M. Frings, C. Bolm, Chem. Soc. Rev. 2007, 36, 55–66;
c) S. T. Diver, A. J. Giessert, Chem. Rev. 2004, 104, 1317–1382.
[8] For metathesis of seleno derivatives, see: a) D. L. J. Clive, H.
Cheng, Chem. Commun. 2001, 605–606; b) D. Tanner, L. Hag-
berg, A. Poulsen, Tetrahedron 1999, 55, 1427–1440.
358.0742; found 358.0786.
(7R,8S)-8-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-4-(hept-1-en-2-
yl)-1-aza-6-selenabicyclo[5.2.0]dec-3-en-9-one (10d): Yield 13.5 mg
1
(59%). H NMR (CDCl3): δ = 0.06 (s, 3 H), 0.07 (s, 3 H), 0.86 (s,
9 H), 0.89 (t, J = 6.9 Hz, 3 H), 1.20 (d, J = 6.3 Hz, 3 H), 1.24–1.37
(m, 4 H), 1.40–1.48 (m, 2 H), 2.23 (t, J = 7.4 Hz, 2 H), 3.15 (dd, J
= 1.7, 3.4 Hz, 1 H), 3.42 (d, J = 13.2 Hz, 1 H), 3.64 (d, J = 13.2 Hz,
1 H), 3.83 (dd, J = 5.7, 16.0 Hz, 1 H), 4.18–4.24 (m, 1 H), 4.30
2
77Se,1H
(dd, J = 5.7, 16.0 Hz, 1 H), 4.99 (s, 1 H), 5.06 (d, J = 1.7, J
= 17.8 Hz, 1 H), 5.10 (s, 1 H), 5.67 (t, J = 6.3 Hz, 1 H) ppm. 13C
NMR (CDCl3): δ = –5.16, –4.22, 14.1, 17.8, 19.3, 22.5, 22.6, 25.6,
28.1, 31.6, 33.8, 39.6, 48.7, 64.7, 68.0, 112.1, 118.2, 145.7, 147.3,
165.4 ppm. IR (CHCl ): ν = 2954, 1760, 1626, 1599, 1462, 1375,
˜
3
1254, 1066, 835 cm–1. MS (EI): m/z = 400 [M – tBu]+. HRMS:
calcd. for C18H30NO2SeSi 400.1211; found 400.1254.
Supporting Information (see also the footnote on the first page of
this article): 1H and 13C NMR spectra of compounds are available.
Acknowledgments
[9] D. R. Garud, D. D. Garud, M. Koketsu, Org. Biomol. Chem.
2009, 7, 2591–2598.
[10] a) H. Ishihara, Y. Hirabayashi, Chem. Lett. 1976, 203–204; b)
H. Ishihara, N. Matsunami, Y. Yamada, Synthesis 1987, 371–
373.
This work was supported by the Ministry of Education, Culture,
Sports, Science and Technology of Japan (Grant-in-Aid for Science
Research, No. 20590005) to which we are grateful.
[11] a) G. L. Sommen, A. Linden, H. Heimgartner, Tetrahedron
Lett. 2005, 46, 6723–6725; b) K. I. Nurbaev, K. A. Zakhidov,
E. O. Oripov, R. A. Smiev, K. M. Shakhidoyatov, Uzb. Khim.
Zh. 1996, 1–2, 96–101; Chem. Abstr. 1996, 126, 47303.
Received: January 16, 2010
[1] a) F. J. Perez-Llarena, G. Bou, Curr. Med. Chem. 2009, 16,
3740–3765; b) S. J. Matthews, J. W. Lancaster, Clin. Ther. 2009,
31, 42–63; c) C. Hubschwerlen, Comprehensive Medicinal
Chemistry II 2006, 7, 479–518; d) A. Bryskier, Expert Rev. Anti-
Infect. Ther. 2005, 3, 505–553.
Published Online: March 23, 2010
Eur. J. Org. Chem. 2010, 2742–2745
© 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
2745