4.4.41.8 β-Silyl Carbonyl Compounds (Update 2013)

Abstract

β-Silyl carbonyl or carboxy compounds are attractive synthetic intermediates. They are important building blocks for various synthetic transformations, thus allowing the construction of more complex molecules. The position of the silyl group far from the carbonyl group allows for numerous transformations on the latter, giving access in some cases to complex natural products. Moreover, the installation of the silyl group on these intermediates in an enantioselective manner has been the subject of numerous investigations, mainly due to its subsequent influence on the adjacent addition of other groups. Finally, the possibility of converting these silyl groups into various other functional groups renders these intermediates valuable tools in the organic chemist’s arsenal.

Key words

β-silyl carbonyl - silylmetalation - hydrosilylation - silyl migration - asymmetric addition

• 1 Colvin EW, In: The Chemistry of Organic Silicon Compounds Rappoport Z, Apeloig Y. Wiley Chichester, UK 1998; 1667

• 2 Hiyama T, Shirakawa E, In: Handbook of Organopalladium Chemistry for Organic Synthesis Negishi E.-i. Wiley Hoboken, NJ 2002; 1. 285

• 3 Denmark SE, Sweis RF, In: Metal-Catalyzed Cross-Coupling Reactions de Meijere A, Diederich F. Wiley-VCH Weinheim, Germany 2004; 1. 163

• 4 Hartmann E, Oestreich M. Angew. Chem. Int. Ed. 2010; 49: 6195

• 5 Inokoishi Y, Sasakura N, Nakano K, Ichikawa Y, Kotsuki H. Org. Lett. 2010; 12: 1616

• 6 Chowdhury R, Ghosh SK. Org. Lett. 2009; 11: 3270

• 7 Yamazaki T, Ishikawa M, Uemura M, Kanda Y, Takei H, Asaoka M. Tetrahedron 2008; 64: 1895

• 8 Balskus EP, Jacobsen EN. J. Am. Chem. Soc. 2006; 128: 6810

• 9 Hartmann E, Vyas DJ, Oestreich M. Chem. Commun. (Cambridge) 2011; 47: 7917

• 10 Fleming I, Barbero A, Walter D. Chem. Rev. 1997; 97: 2063

• 11 Bolze P, Dickmeiss G, Jørgensen KA. Org. Lett. 2008; 10: 3753

• 12 Clark CT, Lake JF, Scheidt KA. J. Am. Chem. Soc. 2004; 126: 84

• 13 Jones GR, Landais Y. Tetrahedron 1996; 52: 7599

• 14 Fleming I, Henning R, Parker DC, Plaut HE, Sanderson PEJ. J. Chem. Soc., Perkin Trans. 1 1995; 317

• 15 Ibrahem I, Santoro S, Himo F, Córdova A. Adv. Synth. Catal. 2011; 353: 245

• 16 Aronica LA, Raffa P, Caporusso AM, Salvadori P. J. Org. Chem. 2003; 68: 9292

• 17 Aronica LA, Raffa P, Valentini G, Caporusso AM, Salvadori P. Eur. J. Org. Chem. 2006; 1845

• 18 Trost BM, Ball ZT. J. Am. Chem. Soc. 2004; 126: 13 942

• 19 Chabaud L, James P, Landais Y. Eur. J. Org. Chem. 2004; 3173

• 20 Suginome M, Ito Y. J. Organomet. Chem. 2003; 685: 218

• 21 Barbero A, Pulido FJ. Acc. Chem. Res. 2004; 37: 817

• 22 Shintani R, Ichikawa Y, Hayashi T, Chen J, Nakao Y, Hiyama T. Org. Lett. 2007; 9: 4643

• 23 Hudrlik PF, Hudrlik AM, Nagendrappa G, Yimenu T, Zellers ET, Chin E. J. Am. Chem. Soc. 1980; 102: 6894

• 24 Hudrlik PF, Hudrlik AM, Yimenu T, Waugh MA, Nagendrappa G. Tetrahedron 1988; 44: 3791

• 25 Fadel A, Vandromme L. Tetrahedron: Asymmetry 1999; 10: 1153

• 26 Trost BM, Ball ZT. J. Am. Chem. Soc. 2005; 127: 17 644

• 27 Stork G, Chan TY. J. Am. Chem. Soc. 1995; 117: 6595

• 28 Stork G, Chan TY, Breault GA. J. Am. Chem. Soc. 1992; 114: 7578

• 29 Lipshutz BH, Tanaka N, Taft BR, Lee C.-T. Org. Lett. 2006; 8: 1963

• 30 Kacprzynski MA, Kazane SA, May TL, Hoveyda AH. Org. Lett. 2007; 9: 3187

• 31 Shintani R, Okamoto K, Hayashi T. Org. Lett. 2005; 7: 4757

• 32 Dieter RK, In: Modern Organocopper Chemistry Krause N. Wiley-VCH Weinheim, Germany 2002; 79

• 33 Fleming I, In: Organocopper Reagents: A Practical Approach Taylor RJK. Oxford University Press Oxford, UK 1995; 257

• 34 Lipshutz BH, Sclafani JA, Takanami T. J. Am. Chem. Soc. 1998; 120: 4021

• 35 Oestreich M, Weiner B. Synlett 2004; 2139

• 36 Tückmantel W, Oshima K, Nozaki H. Chem. Ber. 1986; 119: 1581

• 37 Crump RANC, Fleming I, Urch CJ. J. Chem. Soc., Perkin Trans. 1 1994; 701

• 38 Vaughan A, Singer RD. Tetrahedron Lett. 1995; 36: 5683

• 39 Ager DJ, Fleming I. J. Chem. Soc., Chem. Commun. 1978; 177

• 40 Ager DJ, Fleming I, Patel SK. J. Chem. Soc., Perkin Trans. 1 1981; 2520

• 41 Fleming I, Roessler F. J. Chem. Soc., Chem. Commun. 1980; 276

• 42 Fleming I, Kindon ND. J. Chem. Soc., Chem. Commun. 1987; 1177

• 43 Fleming I, Newton TW. J. Chem. Soc., Perkin Trans. 1 1984; 1805

• 44 Lipshutz BH, Reuter DC, Ellsworth EL. J. Org. Chem. 1989; 54: 4975

• 45 Sharma S, Oehlschlager AC. Tetrahedron 1989; 45: 557

• 46 Sharma S, Oehlschlager AC. J. Org. Chem. 1991; 56: 770

• 47 Hale MR, Hoveyda AH. J. Org. Chem. 1994; 59: 4370

• 48 Palomo C, Aizpurua JM, Iturburu M, Urchegui R. J. Org. Chem. 1994; 59: 240

• 49 Dambacher J, Bergdahl M. Chem. Commun. (Cambridge) 2003; 144

• 50 Dambacher J, Bergdahl M. J. Org. Chem. 2005; 70: 580

• 51 Hayashi T, Matsumoto Y, Ito Y. J. Am. Chem. Soc. 1988; 110: 5579

• 52 Matsumoto Y, Hayashi T, Ito Y. Tetrahedron 1994; 50: 335

• 53 Suginome M, Matsuda T, Ito Y. Organometallics 2000; 19: 4647

• 54 Suginome M, Ohmori Y, Ito Y. J. Organomet. Chem. 2000; 611: 403

• 55 Walter C, Auer G, Oestreich M. Angew. Chem. Int. Ed. 2006; 45: 5675

• 56 Walter C, Fröhlich R, Oestreich M. Tetrahedron 2009; 65: 5513 145

• 57 Calderone JA, Santos WL. Org. Lett. 2012; 14: 2090

• 58 Lee K.-s, Hoveyda AH. J. Am. Chem. Soc. 2010; 132: 2898

• 59 Walter C, Oestreich M. Angew. Chem. Int. Ed. 2008; 47: 3818

• 60 Welle A, Petrignet J, Tinant B, Wouters J, Riant O. Chem.–Eur. J. 2010; 16: 10 980

• 61 Ohmura T, Taniguchi H, Kondo Y, Suginome M. J. Am. Chem. Soc. 2007; 129: 3518

• 62 Matsuda I, Takeuchi K, Itoh K. Tetrahedron Lett. 1999; 40: 2553

• 63 Fujiwara T, Sawabe K, Takeda T. Tetrahedron 1997; 53: 8349

• 64 Rendler S, Oestreich M. Angew. Chem. Int. Ed. 2007; 46: 498

• 65 Deutsch C, Krause N, Lipshutz BH. Chem. Rev. 2008; 108: 2916

• 66 Appella DH, Moritani Y, Shintani R, Ferreira EM, Buchwald SL. J. Am. Chem. Soc. 1999; 121: 9473

• 67 Moritani Y, Appella DH, Jurkauskas V, Buchwald SL. J. Am. Chem. Soc. 2000; 122: 6797

• 68 Jurkauskas V, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 2892

• 69 Lipshutz BH, Frieman BA, Tomaso Jr AE. Angew. Chem. Int. Ed. 2006; 45: 1259

• 70 Hughes G, Kimura M, Buchwald SL. J. Am. Chem. Soc. 2003; 125: 11 253

• 71 Lipshutz BH, Servesko JM, Taft BR. J. Am. Chem. Soc. 2004; 126: 8352

• 72 Rainka MP, Milne JE, Buchwald SL. Angew. Chem. Int. Ed. 2005; 44: 6177

• 73 Llamas T, Arrayás RG, Carretero JC. Angew. Chem. Int. Ed. 2007; 46: 3329

• 74 Czekelius C, Carreira EM. Angew. Chem. Int. Ed. 2003; 42: 4793

• 75 Czekelius C, Carreira EM. Org. Lett. 2004; 6: 4575

• 76 Rupnicki L, Saxena A, Lam HW. J. Am. Chem. Soc. 2009; 131: 10 386

• 77 Shintani R, Takatsu K, Hayashi T. Angew. Chem. Int. Ed. 2007; 46: 3735

• 78 Mitchell TN, Schütze M, Gießelmann F. Synlett 1997; 183

• 79 Mitchell TN, Schütze M. Tetrahedron 1999; 55: 1285

• 80 Nakazaki A, Nakai T, Tomooka K. Angew. Chem. Int. Ed. 2006; 45: 2235

• 81 Sparks MA, Panek JS. J. Org. Chem. 1991; 56: 3431

• 82 Carlier PR, Mungall WS, Schroder G, Sharpless KB. J. Am. Chem. Soc. 1988; 110: 2978

• 83 Song Z, Lei Z, Gao L, Wu X, Li L. Org. Lett. 2010; 12: 5298