An Update on Catalytic Strategies for the Synthesis of α-Hydroxyketones

Abstract

The catalytic asymmetric synthesis of α-oxygenated ketones is still a challenge to modern methodology. This SYNPACTS gives an overview on recent developments in this area and besides direct α-oxidation protocols, alternative strategies that make use of redox-neutral or reductive conditions are discussed.

Key words

asymmetric catalysis - cross-coupling - cyclization - ketones - oxygenations

• References

• 1a Smith AM. R, Hii KK. Chem. Rev. 2011; 111: 1637
• 1b Janey JM. Angew. Chem. Int. Ed. 2005; 44: 4292
• 1c Plietker B. Tetrahedron: Asymmetry 2005; 16: 3453

For selected recent examples, see:
• 2a Lu M, Zhu D, Lu Y, Zeng X, Tan B, Xu Z, Zhong G. J. Am. Chem. Soc. 2009; 131: 4562
• 2b Smith AM. R, Billen D, Hii KK. Chem. Commun. 2009; 3925
• 3 Davis FA, Chen B.-C. Chem. Rev. 1992; 92: 919
• 4a Yanagisawa A, Takeshita S, Izumi Y, Yoshida K. J. Am. Chem. Soc. 2010; 132: 5328
• 4b Momiyama N, Yamamoto H. J. Am. Chem. Soc. 2003; 125: 6038
• 4c Momiyama N, Yamamoto H. Angew. Chem. Int. Ed. 2002; 41: 2986
• 5 Merino P, Tejero T. Angew. Chem. Int. Ed. 2004; 43: 2995
• 6a Ramachary DB, Barbas CF. III. Org. Lett. 2005; 7: 1577
• 6b Hayashi Y, Yamaguchi J, Sumiya T, Shoji M. Angew. Chem. Int. Ed. 2004; 43: 1112
• 6c Bøgevig A, Sundén H, Córdova A. Angew. Chem. Int. Ed. 2004; 43: 1109
• 7 Sundén H, Engqvist M, Casas J, Ibrahem I, Córdova A. Angew. Chem. Int. Ed. 2004; 43: 6532
• 8a Tanaka A, Moriyama K, Togo H. Synlett 2011; 1853
• 8b Chen C, Feng X, Zhang G, Zhao Q, Huang G. Synthesis 2008; 3205
• 8c Sheng J, Li X, Tang M, Gao B, Huang G. Synthesis 2007; 1165
• 8d Yamamoto Y, Togo H. Synlett 2006; 798
• 8e Engqvist M, Casas J, Sundén H, Ibrahem I, Córdova A. Tetrahedron Lett. 2005; 46: 2053
• 9a Hamed OA, El-Qisairi A, Qaseer H, Hamed EM, Henry PM, Becker DP. Tetrahedron Lett. 2012; 53: 2699
• 9b El-Qisairi AK, Qaseer HA. J. Organomet. Chem. 2002; 659: 50
• 10 Cotton FA, Gu J, Murillo CA, Timmons DJ. J. Am. Chem. Soc. 1998; 120: 13280
• 11 Chuang GJ, Wang W, Lee E, Ritter T. J. Am. Chem. Soc. 2011; 133: 1760
• 12 Arai T, Sato T, Noguchi H, Kanoh H. Chem. Lett. 2006; 35: 1094
• 13a Plietker B. Eur. J. Org. Chem. 2005; 1919
• 13b Plietker B. J. Org. Chem. 2004; 69: 8287
• 13c Plietker B, Niggemann M. Org. Biomol. Chem. 2004; 2: 2403
• 13d Plietker B. Org. Lett. 2004; 6: 289
• 13e Plietker B. J. Org. Chem. 2003; 68: 7123
• 14a Minato D, Arimoto H, Nagasue Y, Demizu Y, Onomura O. Tetrahedron 2008; 64: 6675
• 14b Onomura O, Arimoto H, Matsumura Y, Demizu Y. Tetrahedron Lett. 2007; 48: 8668
• 15a Müller CE, Hrdina R, Wende RC, Schreiner PR. Chem.–Eur. J. 2011; 17: 6309
• 15b Müller CE, Zell D, Schreiner PR. Chem.–Eur. J. 2009; 15: 9647

For selected references, see:
• 16a Lu Y, Woo SK, Krische MJ. J. Am. Chem. Soc. 2011; 133: 13876
• 16b Cho C.-W, Krische MJ. Org. Lett. 2006; 8: 891
• 16c Jang H.-Y, Huddleston RR, Krische MJ. J. Am. Chem. Soc. 2004; 126: 4664
• 16d Huddleston RR, Jang H.-Y, Krische MJ. J. Am. Chem. Soc. 2003; 125: 11488
• 16e Jang H.-Y, Huddleston RR, Krische MJ. Angew. Chem. Int. Ed. 2003; 42: 4074
• 17a Feng X, Nie Y, Yang J, Du H. Org. Lett. 2012; 14: 624
• 17b Ganci GR, Chisholm JD. Tetrahedron Lett. 2007; 48: 8266
• 17c Oi S, Moro M, Furuhara H, Kawanishi T, Inoue Y. Tetrahedron 2003; 59: 4351
• 18 Linghu X, Johnson JS. Angew. Chem. Int. Ed. 2003; 42: 2534
• 19a Bugaut X, Glorius F. Chem. Soc. Rev. 2012; 41: 3511
• 19b Biju AT, Kuhl N, Glorius F. Acc. Chem. Res. 2011; 44: 1182
• 19c Enders D, Grossmann A, Fronert J, Raabe G. Chem. Commun. 2010; 46: 6282
• 19d Enders D, Niemeier O, Henseler A. Chem. Rev. 2007; 107: 5606
• 19e Marion N, Díez-González S, Nolan SP. Angew. Chem. Int. Ed. 2007; 46: 2988
• 19f Takikawa H, Hachisu Y, Bode JW, Suzuki K. Angew. Chem. Int. Ed. 2006; 45: 3492
• 19g Enders D, Niemeier O, Balensiefer T. Angew. Chem. Int. Ed. 2006; 45: 1463
• 19h Dudding T, Houk KN. Proc. Natl. Acad. Sci. 2004; 101: 5770
• 19i Enders D, Kallfass U. Angew. Chem. Int. Ed. 2002; 41: 1743
• 19j Enders D, Breuer K, Teles JH. Helv. Chim. Acta 1996; 79: 1217
• 20a Lehwald P, Richter M, Röhr C, Liu H.-W, Müller M. Angew. Chem. Int. Ed. 2010; 49: 2389
• 20b Dünkelmann P, Kolter-Jung D, Nitsche A, Demir AS, Siegert P, Lingen B, Baumann M, Pohl M, Müller M. J. Am. Chem. Soc. 2002; 124: 12084

For selected examples, see:
• 21a Streuff J. Chem.–Eur. J. 2011; 17: 5507
• 21b Blümke TD, Piller FM, Knochel P. Chem. Commun. 2010; 46: 4082
• 21c Yoho CW, Levine R. J. Am. Chem. Soc. 1952; 74: 5597
• 22a Guijarro D, Mancheño B, Yus M. Tetrahedron 1993; 49: 1327
• 22b Cheng K.-F, Li P.-C. Synth. Commun. 1977; 7: 423
• 22c Ioffe DV. Zh. Obshch. Khim. 1965; 35: 1851
• 23 Corey EJ, Pyne SG. Tetrahedron Lett. 1983; 24: 2821

For selected references, see:
• 24a Miyazaki T, Maekawa H, Yonemura K, Yamamoto Y, Yamanaka Y, Nishiguchi I. Tetrahedron 2011; 67: 1598
• 24b Kise N, Agui S, Morimoto S, Ueda N. J. Org. Chem. 2005; 70: 9407
• 24c Yamamoto Y, Matsumi D, Hattori R, Itoh K. J. Org. Chem. 1999; 64: 3224
• 24d Molander GA, Wolfe CN. J. Org. Chem. 1998; 63: 9031
• 24e Shono T, Kise N. Tetrahedron Lett. 1990; 31: 1303
• 24f Kraus GA, Sy JO. J. Org. Chem. 1989; 54: 77
• 24g Hou Z, Takamine K, Aoki O, Shiraishi H, Fujiwara Y, Taniguchi H. J. Chem. Soc., Chem. Commun. 1988; 668
• 25a Nicolaou KC, Ellery SP, Chen JS. Angew. Chem. Int. Ed. 2009; 48: 7140
• 25b Edmonds DJ, Johnston D, Procter DJ. Chem. Rev. 2004; 104: 3371
• 26 Zhou L, Hirao T. Tetrahedron 2001; 57: 6927

For selected reviews, see:
• 27a Hirao T. Top. Curr. Chem. 2007; 279: 53
• 27b Gansäuer A, Bluhm H. Chem. Rev. 2000; 100: 2771
• 27c Fürstner A, Bogdanović B. Angew. Chem. Int. Ed. 1996; 35: 2442
• 28 Streuff J, Feurer M, Bichovski P, Frey G, Gellrich U. Angew. Chem. Int. Ed. 2012; 51: 8661
• 29 Fernández-Mateos A, Teijón PH, Burón LM, Clemente RR, González RR. J. Org. Chem. 2007; 72: 9973