Communication
Organic & Biomolecular Chemistry
thank B. Seetharamsingh (CSIR-NCL, Pune) for his help in
some of the initial experiments. RR thanks CSIR, New Delhi,
for the award of a research fellowship.
2010, 695, 310–313; ( j) U. Olszewski, R. Zeillinger,
M. D. Kars, A. Zalatnai, J. Molnar and G. Hamilton, Anti-
Cancer Agents Med. Chem., 2012, 12, 663–671.
5 Unpublished results. However, a PCT document covering
Silinezolid and related compounds is available in public
domain. D. S. Reddy, B. Seetharamsingh and R. Ramesh,
WO, 054275, A1, 2013.
Notes and references
6 Selected reviews and publications on allylsilanes:
(a) H. Sakurai, Pure Appl. Chem., 1982, 54, 1–22;
(b) A. Hosomi, Acc. Chem. Res., 1988, 21, 200–206;
(c) J. R. Hwu, B.-L. Chen and S.-S. Shiao, J. Org. Chem.,
1995, 60, 2448–2455; (d) S. BouzBouz, L. Boulard and
J. Cossy, Org. Lett., 2007, 9, 3765–3768; (e) T. H. Chan and
D. Wang, Chem. Rev., 1995, 95, 1279–1292; (f) C. E. Masse
and J. S. Panek, Chem. Rev., 1995, 95, 1293–1316; (g) J. Wu,
Y. Chen and J. S. Panek, Org. Lett., 2010, 12, 2112–2115;
(h) R. E. Grote and E. R. Jarvo, Org. Lett., 2009, 11, 485–488;
(i) J. W. A. Kinnaird, P. Y. Ng, K. Kubota, X. Wang and
J. L. Leighton, J. Am. Chem. Soc., 2002, 124, 7920–7921;
( j) J. S. Panek and M. Yang, J. Am. Chem. Soc., 1991, 113,
9868–9870.
7 (a) S. D. Rosenberg, J. J. Walburn and H. E. Ramsden,
J. Org. Chem., 1957, 22, 1606–1607; (b) R. E. Scott and
K. C. Frisch, J. Am. Chem. Soc., 1951, 73, 2599–
2600.
8 Z. Li, C. Yang, H. Zheng, H. Qiu and G. Lai, J. Organomet.
Chem., 2008, 693, 3771–3779.
1 Selected reviews and publications: (a) R. West and
T. J. Barton, J. Chem. Educ., 1980, 57, 165–169;
(b) I. Fleming, Chem. Soc. Rev., 1981, 10, 83–111;
(c) G. L. Larson, Recent Synthetic Applications of Organo-
silanes, in Organic Silicon Compounds, 2004, vol. 1 and 2;
(d) S. E. Denmark and R. F. Sweis, Chem. Pharm. Bull.,
2002, 50, 1531–1541; (e) S. E. Denmark and C. S. Regens,
Acc. Chem. Res., 2008, 41, 1486–1499; (f) M. A. Brook,
Silicon in Organic, Organometallic and Polymer Chemistry,
Wiley Interscience, New York, 2000; (g) I. Fleming, in Com-
prehensive Organic Synthesis, ed. B. M. Trost and I. Fleming,
Pergamon Press, Oxford, 1991, vol. 2, pp. 563–593;
(h) H.-J. Zhang, D. L. Priebbenow and C. Bolm, Chem. Soc.
Rev., 2013, 42, 8540–8571.
2 Selected references related to silicon based polymers:
(a) D. Y. Son, Chem. Commun., 2013, 49, 10209–10210;
(b) S. Thames and K. Panjnani, J. Inorg. Organomet. Polym.,
1996, 6, 59–94; (c) R. Richter, G. Roewer, U. Böhme,
K. Busch, F. Babonneau, H. P. Martin and E. Müller, Appl.
Organomet. Chem., 1997, 11, 71–106 and references cited
therein.
9 Z. Li, X. Cao, G. Lai, J. Liu, Y. Ni, J. Wu and H. Qiu,
J. Organomet. Chem., 2006, 691, 4740–4746.
3 See selected recent reviews and publications for the use of 10 Only once Zn was utilized in the literature for the allylation
silicon in medicinal chemistry: (a) J. S. Mills and
G. A. Showell, Drug Discovery Today, 2003, 8, 551–556;
(b) J. S. Mills and G. A. Showell, Expert Opin. Invest. Drugs,
of chlorosilanes, but it was not generalized. See: T. Sanji,
M. Iwata, M. Watanabe, T. Hoshi and H. Sakurai, Organo-
metallics, 1998, 17, 5068–5071.
2004, 13, 1149–1157; (c) S. Gately and R. West, Drug Dev. 11 (a) G. Cravotto, E. C. Gaudino and P. Cintas, Chem. Soc.
Res., 2007, 68, 156–163; (d) A. K. Franz and S. O. Wilson,
J. Med. Chem., 2013, 56, 388–405; (e) R. Tacke, Angew.
Rev., 2013, 42, 7521–7534; (b) C. Einhorn, J. Einhorn and
J.-L. Luche, Synthesis, 1989, 787–813.
Chem., 1999, 111, 3197–3200, (Angew. Chem., Int. Ed., 1999, 12 N. Voloshchuk and J. K. Montclare, Mol. BioSyst., 2010, 6,
38, 3015–3018). 65.
4 Selected recent reports on silicon switch approach: 13 (a) D. A. Dougherty, Curr. Opin. Chem. Biol., 2000, 4, 645–
(a) M. Chang, S.-R. Park, J. Kim, M. Jang, J. H. Park,
J. E. Park, H.-G. Park, Y.-G. Suh, Y. S. Jeong, Y.-H. Park and
H.-D. Kim, Bioorg. Med. Chem., 2010, 18, 111–116;
652; (b) M. Tanaka, K. Anan, Y. Demizu, M. Kurihara,
M. Doi and H. Suemune, J. Am. Chem. Soc., 2005, 127,
11570–11571.
(b) K. Maruyama, M. Nakamura, S. Tomoshige, K. Sugita, 14 (a) M. Mortensen, R. Husmann, E. Veri and C. Bolm, Chem.
M. Makishima, Y. Hashimoto and M. Ishikawa, Bioorg.
Med. Chem. Lett., 2013, 23, 4031–4036; (c) M. Nakamura,
M. Makishima and Y. Hashimoto, Bioorg. Med. Chem. Lett.,
2013, 21, 1643–1651; (d) M. Nakamura, D. Kajita,
Y. Matsumoto and Y. Hashimoto, Bioorg. Med. Chem. Lett.,
2013, 21, 7381–7391; (e) M. Fischer and R. Tacke, Organo-
metallics, 2013, 32, 7181–7185; (f) J. Wang, C. Ma, Y. Wu,
R. A. Lamb, L. H. Pinto and W. F. DeGrado, J. Am. Chem.
Soc., 2011, 133, 13844–13847; (g) P. Luger, M. Weber,
C. Hübschle and R. Tacke, Org. Biomol. Chem., 2013, 11,
2348–2354; (h) A. P. Ayscough, G. A. Showell, M. R. Teall,
H. E. Temple and S. Ahmed, WO, 092342, A1, 2010;
(i) D. Troegel, F. Möller and R. Tacke, J. Organomet. Chem.,
Soc. Rev., 2009, 38, 1002–1010; (b) R. J. Smith and S. Bienz,
Helv. Chim. Acta, 2004, 87, 1681–1696; (c) R. Tacke,
M. Merget, R. Bertermann, M. Bernd, T. Beckers and
T. Reissmann, Organometallics, 2000, 19, 3486–3497;
(d) B. Vivet, F. Cavelier and J. Martinez, Eur. J. Org. Chem.,
2000, 807–811; (e) R. D. Walkup, D. C. Cole and
B. R. Whittlesey, J. Org. Chem., 1995, 60, 2630–2634;
(f) S. Falgner, G. Buchner and R. Tacke, J. Organomet.
Chem., 2010, 695, 2614–2617; (g) S. Dörrich, S. Falgner,
S. Schweeberg, C. Burschka, P. Brodin, B. M. Wissing,
B. Basta, P. Schell, U. Bauer and R. Tacke, Organometallics,
2012, 31, 5903–5917; (h) S. Falgner, C. Burschka,
S. Wagner, A. Böhm, J. O. Daiss and R. Tacke, Organo-
4096 | Org. Biomol. Chem., 2014, 12, 4093–4097
This journal is © The Royal Society of Chemistry 2014