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Synlett 2013; 24(2): 139-144
DOI: 10.1055/s-0032-1317706
DOI: 10.1055/s-0032-1317706
synpacts
Exploration of Versatile Geminal Bis(silane) Chemistry
Further Information
Publication History
Received: 03 September 2012
Accepted after revision: 01 November 2012
Publication Date:
28 November 2012 (online)
Abstract
Geminal bis(silyl) compounds, a special type of organosilane, are attractive synthons because of their great potential for bifunctional reactivity. This article outlines our recent efforts to develop a practical method to synthesize geminal bis(silane) compounds and to explore their interesting bifunctionality.
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References and Notes
- 1a Overman LE, Blumenkopf TA. Chem. Rev. 1986; 86: 857
- 1b Panek M, Masse CE. Chem. Rev. 1995; 95: 1293
- 1c Langkopf E, Schinzer D. Chem. Rev. 1995; 95: 1375
- 1d Fleming I, Barbero A, Walter D. Chem. Rev. 1997; 97: 2063
- 2a Brook AG. Acc. Chem. Res. 1974; 7: 77
- 2b Moser WH. Tetrahedron 2001; 57: 2065
- 3a Danheiser RL, Carini DJ, Basak A. J. Am. Chem. Soc. 1981; 103: 1604
- 3b Danheiser RL, Kwasigroch CA, Tsai YM. J. Am. Chem. Soc. 1985; 107: 7233
- 3c Danheiser RL, Fink DM, Tsai YM. Org. Synth. 1988; 66: 8
- 3d Danheiser RL, Stoner EJ, Koyama H, Yamashita DS, Klade CA. J. Am. Chem. Soc. 1989; 111: 4407
- 3e Danheiser RL, Dixon BR, Gleason RW. J. Org. Chem. 1992; 57: 6094
- 4a Tamao K, Akita M, Kumada M. J. Organomet. Chem. 1983; 254: 13
- 4b Fleming I, Henning R, Plaut H. J. Chem. Soc., Chem. Commun. 1984; 29
- 4c For the latest review on Fleming–Tamao oxidation, see: Jones GR, Landais Y. Tetrahedron 1996; 52: 7599
- 5a Hatanaka Y, Hiyama T. J. Org. Chem. 1988; 53: 918
- 5b For the latest review on Hiyama coupling, see: Denmark S, Regens CS. Acc. Chem. Res. 2008; 41: 1486
- 6a Peterson DJ. J. Org. Chem. 1968; 33: 780
- 6b For the latest review on Peterson olefination, see: van Staden LF, Gravestock D, Ager DJ. Chem. Soc. Rev. 2002; 31: 195
- 7a Hosomi A, Endo M, Sakurai H. Chem. Lett. 1976; 941
- 7b Fleming I. Allylsilanes, Allylstannanes and Related Systems . In Comp. Org. Synth. . Vol. 6. Trost BM, Fleming I. Pergamon Press; Oxford: 1991: 563-593
- 7c Schinzer D. Synthesis 1988; 263
- 7d Fleming I, Dunogues J, Smithers R. Org. React. 1989; 37: 57
- 8a Fleming I, Floyd CD. J. Chem. Soc., Perkin Trans. 1 1981; 969
- 8b Ahlbrecht H, Farnung W, Simon H. Chem. Ber. 1984; 117: 2622
- 8c Brook AG, Chrusciel JJ. Organometallics 1984; 3: 1317
- 8d Klumpp GW, Mierop AJ. C, Vrielink JJ, Brugman A, Schakel M. J. Am. Chem. Soc. 1985; 107: 6740
- 8e Lautens M, Delanghe PH. M, Goh JB, Zhang CH. J. Org. Chem. 1995; 60: 4213
- 8f Lautens M, Ben RN, Delanghe PH. M. Tetrahedron 1996; 52: 7221
- 8g Princet B, Anselme G, Pornet J. Synth. Commun. 1999; 29: 3326
- 8h Princet B, Gariglio HG, Pornet J. J. Organomet. Chem. 2000; 604: 186
- 8i Hodgson DM, Barker SF, Mace LH, Moran JR. Chem. Commun. 2001; 153
- 8j Onyeozili EN, Maleczka RE. Tetrahedron Lett. 2006; 47: 6565
- 9a Marek I, Normant JF. Chem. Rev. 1996; 96: 3241
- 9b Marshall JA. Chem. Rev. 1996; 96: 31
- 9c Marek I. Chem. Rev. 2000; 100: 2887
- 10 Lautens M, Ben RN, Delanghe PH. M. Angew. Chem. Int. Ed. Engl. 1994; 33: 2448
- 11 Williams DR, Morales-Ramos ÁI, Williams CM. Org. Lett. 2006; 8: 4393
- 12a Simpkins SM. E, Kariuki BM, Arico CS, Cox LR. Org. Lett. 2003; 5: 3971
- 12b Nahm MR, Xin LH, Potnick JR, Yates CM, White PS, Johnson JS. Angew. Chem. Int. Ed. 2005; 44: 2377
- 12c Yamago S, Fujita K, Miyoshi M, Kotani M, Yoshida J. Org. Lett. 2005; 7: 909
- 12d Mori H, Matsuo T, Yoshioka Y, Katsumura S. J. Org. Chem. 2006; 71: 9004
- 12e Mori Y, Futamura Y, Horisaki K. Angew. Chem. Int. Ed. 2008; 47: 1091
- 13a Mitchell TN, Schütze M, Giebelmann F. Synlett 1997; 187
- 13b Mitchell TN, Schütze M. Tetrahedron 1999; 55: 1285
- 14 Song ZL, Lei Z, Gao L, Wu X, Li LJ. Org. Lett. 2010; 12: 5298
- 15 Gao L, Lin XL, Lei J, Song ZL, Lin Z. Org. Lett. 2012; 14: 158
- 16a Smith AB. III, Adams CM. Acc. Chem. Res. 2004; 37: 365
- 16b Smith AB. III, Wuest WM. Chem. Commun. 2008; 5883
- 16c Smith AB. III, Kim WS. Proc. Natl. Acad. Sci. U.S.A. 2011; 108: 6787
- 16d Smith AB. III, Tong RB, Kim WS, Maio WA. Angew. Chem. Int. Ed. 2011; 50: 8904
- 16e Smith AB. III, Han H, Kim WS. Org. Lett. 2011; 13: 3328
- 16f Smith AB. III, Hoye AT, Martinez-Solorio D, Kim W.-S, Tong RB. J. Am. Chem. Soc. 2012; 134: 4533
- 17 Sun XW, Lei J, Sun CZ, Song ZL, Yan LJ. Org. Lett. 2012; 14: 1094
- 18a Taguchi H, Ghoroku K, Tadaki M, Tsubouchi A, Takeda T. Org. Lett. 2001; 3: 3811
- 18b Smith AB. III, Kim WS, Tong RB. Org. Lett. 2010; 12: 588
- 19a Hale KJ, Hummersone MG, Manaviazar S, Frigerio M. Nat. Prod. Rep. 2002; 19: 413
- 19b Kortmansky J, Schwartz GK. Cancer Invest. 2003; 21: 924
- 19c Wender PA, Baryza JL, Hilinski MK, Horan JC, Kan C, Verma VA. Beyond Natural Products: Synthetic Analogues of Bryostatin 1 . In Drug Discovery Research: New Frontiers in the Post-Genomic Era . Huang Z. Wiley-VCH; Weinheim: 2007: 127-162
- 19d Hale KJ, Manaviazar S. Chem.–Asian J. 2010; 5: 704
- 20 Lu J, Song ZL, Zhang YB, Gan ZB, Li HZ. Angew. Chem. Int. Ed. 2012; 51: 5367
- 21 For the latest review on Prins cyclization, see: Crane EA, Scheidt KA. Angew. Chem. Int. Ed. 2010; 49: 8316
- 22 The geminal bis(silyl) homoallylic alcohols 19 were synthesized in 55–60% yield by a zinc-promoted Barbier reaction of aldehyde with bis(silyl) allyl bromide, which was prepared from bis(silyl) enal 11 in three steps. See the Supporting Information of ref. 15 for details.
For selective reviews on organosilanes, see:
For reviews on the Brook rearrangement, see:
For reviews on Sakurai allylation, see:
For studies on geminal bis(silyl) species, see:
For reviews on geminal bimetallic species, see:
For recent studies on the retro-[1,4] Brook rearrangement, see:
For reviews on anion relay chemistry (ARC), see:
For the latest advances, see:
For reviews on the bryostatins, see: