Synlett 2012; 23(14): 1999-2004
DOI: 10.1055/s-0032-1316738
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© Georg Thieme Verlag Stuttgart · New York

Challenges and Achievements in the Transition-Metal-Catalyzed Asymmetric α-Arylation of Aldehydes

Clément Mazet*
Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva 4, Switzerland, Fax: +41(22)3796288   Email: clement.mazet@unige.ch
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Further Information

Publication History

Received: 12 June 2012

Accepted after revision: 02 July 2012

Publication Date:
08 August 2012 (online)


Abstract

The direct enantioselective α-arylations of linear and α-branched aldehydes are faced by different but equally difficult challenges. This account covers the most recent contributions in this exciting field of research.

 
  • References

    • 1a Semmelhack MF, Stauffer RD, Rogerson TD. Tetrahedron Lett. 1973; 14: 4519
    • 1b Semmelhack MF, Chong BP, Stauffer RD, Rogerson TD, Chong A, Jones LD. J. Am. Chem. Soc. 1975; 97: 2507

      For reviews on metal-catalyzed α-arylation of carbonyls, see:
    • 2a Lloyd-Jones GC. Chem.–Eur. J. 2002; 41: 954
    • 2b Culkin DA, Hartwig JF. Acc. Chem. Res. 2003; 36: 234
    • 2c Bortoloso AC. B. Synlett 2009; 320
    • 2d Johansson CC. C, Colacot TJ. Angew. Chem. Int. Ed. 2010; 49: 676
    • 2e Bellina F, Rossi R. Chem. Rev. 2010; 110: 1082

      For recent reviews on asymmetric hydroformylation, see:
    • 3a Nozaki K In Comprehensive Asymmetric Catalysis . Vol. 1. Jacobsen EN, Pfaltz A, Yamamoto H. Springer; Berlin: 1999. Chap. 11
    • 3b Claver C, van Leuween PW. N. M In Rhodium-Catalyzed Hydroformy-lation . van Leuween PW. N. M, Claver C. Kluwer Academic Publishers; Dodrecht: 2000. Chap. 5
    • 3c Guai A, Godard C, Castillón S, Claver C. Tetrahedron: Asymmetry 2004; 15: 1135
    • 3d Klosin J, Landis CR. Acc. Chem. Res. 2007; 40: 1251

    • For recent examples of asymmetric hydroformylation:
    • 3e Worthy AD, Joe CL, Lightburn TE, Tan KL. J. Am. Chem. Soc. 2010; 132: 14757
    • 3f McDonald RI, Wong GW, Neupane RP, Stahl SS, Landis CR. J. Am. Chem. Soc. 2010; 132: 14027
    • 3g Watkins AL, Landis CR. Org. Lett. 2011; 13: 164

      For recent reviews on enamine and SOMO catalyses, see:
    • 4a Mukherjee S, Yang JW, Hoffmann S, List B. Chem. Rev. 2007; 107: 5471
    • 4b Melchiorre P, Marigo M, Carlone A, Bartoli G. Angew. Chem. Int. Ed. 2008; 47: 6138
    • 4c MacMillan DW. C. Nature (London) 2008; 455: 304
    • 4d Bertelsen S, Jørgensen KA. Chem. Soc. Rev. 2009; 38: 2178
    • 4e Melchiorre P. Angew. Chem. Int. Ed. 2009; 48: 1360

    • For selected recent examples, see:
    • 4f Beeson TD, Mastracchio A, Hong J.-B, Ashton K, MacMillan DW. C. Science 2007; 316: 582
    • 4g Enders D, Wang C, Bats JW. Angew. Chem. Int. Ed. 2008; 47: 7539
    • 4h Nicewicz DA, MacMillan DW. C. Science 2008; 322: 77
    • 4i Shaikh RR, Mazzanti A, Petrini M, Bartoli G, Melchiorre P. Angew. Chem. Int. Ed. 2008; 47: 8707
    • 4j Conrad JC, Kong J, Laforteza BN, MacMillan DW. C. J. Am. Chem. Soc. 2009; 131: 11640
    • 4k Um JM, Gutierrez O, Schoenebeck F, Houk KN, MacMillan DW. C. J. Am. Chem. Soc. 2010; 132: 6001
  • 5 Galarini R, Musco A, Pontellini R, Santi R. J. Mol. Catal. 1992; 72: L11
  • 6 Åhman J, Wolfe JP, Troutman MV, Palucki M, Buchwald SL. J. Am. Chem. Soc. 1998; 120: 1918

    • For recent examples on the asymmetric α-arylation of ketones, see:
    • 7a Fox JM, Huang X, Chieffi A, Buchwald SL. J. Am. Chem. Soc. 2000; 122: 1360
    • 7b Hamada T, Chieffi A, Åhman J, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 1261
    • 7c Chen G, Kwong FY, Chan HO, Yu W.-Y, Chan AS. C. Chem. Commun. 2006; 1413
    • 7d Liao X, Weng Z, Hartwig JF. J. Am. Chem. Soc. 2008; 130: 195
    • 7e Ge S, Hartwig JF. J. Am. Chem. Soc. 2011; 133: 16330

      For recent examples on the asymmetric α-arylation of esters, see:
    • 8a Spielvogel DJ, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 3500
    • 8b Spielvogel DJ, Davis WM, Buchwald SL. J. Am. Chem. Soc. 2002; 121: 3833
    • 8c Liu XHartwig J. F. J. Am. Chem. Soc. 2004; 126: 5182

    • For diastereoselective reactions, see:
    • 8d Bercot EA, Caille S, Bostick TM, Ranganathan K, Jensen R, Faul MM. Org. Lett. 2008; 10: 5251
    • 8e Jiang L, Weist S, Jansat S. Org. Lett. 2009; 11: 1543

      For recent examples on the asymmetric α-arylation of amides to form quaternary stereocenters, see:
    • 9a Lee S, Hartwig JF. J. Org. Chem. 2001; 66: 3402
    • 9b Aaro T, Kondo K, Aoyama T. Tetrahedron Lett. 2006; 47: 1417
    • 9c Kündig EP, Seidel TM, Jia Y.-X, Bernardinelli G. Angew. Chem. Int. Ed. 2007; 46: 8484
    • 9d Luan X, Mariz R, Robert C, Gatti M, Blumentritt S, Linden A, Dorta R. Org. Lett. 2008; 10: 5569
    • 9e Würtz S, Lohre C, Fröhlich R, Bergander K, Glorius F. J. Am. Chem. Soc. 2009; 131: 8344
    • 9f Luan X, Wu L, Drinkel E, Mariz R, Gatti M, Dorta R. Org. Lett. 2010; 12: 1912
    • 9g Jia Y.-X, Katayev D, Bernardinelli G, Seidel TM, Kündig EP. Chem.–Eur. J. 2010; 16: 6300
    • 9h Liu L, Ishida N, Ashida S, Murakami M. Org. Lett. 2011; 13: 1666
  • 10 A single intermolecular asymmetric α-arylation of amides has been reported to date: Taylor AM, Altman RA, Buchwald SL. J. Am. Chem. Soc. 2009; 131: 9900
    • 11a Dai X, Strotman NA, Fu GC. J. Am. Chem. Soc. 2008; 130: 3302
    • 11b Lundin PM, Esquivias J, Fu GC. Angew. Chem. Int. Ed. 2009; 48: 154
    • 11c Lou S, Fu GC. J. Am. Chem. Soc. 2010; 132: 1264
    • 11d Lundin PM, Fu GC. J. Am. Chem. Soc. 2010; 132: 11028
  • 12 Bigot A, Williamson AE, Gaunt MJ. J. Am. Chem. Soc. 2011; 133: 13778
  • 13 Harvey JS, Simonovich SP, Jamison CR, MacMillan DW. C. J. Am. Chem. Soc. 2011; 133: 13782
  • 14 Huang Z, Liu Z, Zhou J. J. Am. Chem. Soc. 2011; 133: 15882
  • 15 Kobayashi K, Yamamoto Y, Miyaura N. Organometallics 2011; 30: 6323
  • 16 Allen AE, MacMillan DW. C. J. Am. Chem. Soc. 2011; 133: 4260
    • 17a Kalyani D, Deprez NR, Desai LV, Sanford M. J. Am. Chem. Soc. 2005; 127: 7330
    • 17b Phipps RJ, Grimster NP, Gaunt MJ. J. Am. Chem. Soc. 2008; 130: 8172
  • 18 Skucas E, MacMillan DW. C. J. Am. Chem. Soc. 2012; 134: 9090

    • For seminal contributions, see:
    • 19a Muratake H, Nakai H. Tetrahedron Lett. 1999; 40: 2355
    • 19b Muratake H, Natsume M. Tetrahedron Lett. 2002; 43: 2913
    • 19c Terao Y, Fukuoka Y, Satoh T, Miura M, Nomura M. Tetrahedron Lett. 2002; 43: 101
    • 19d Muratake H, Natsume M, Nakai H. Tetrahedron 2004; 60: 11783

    • For general and recent methods, see:
    • 19e Vo GD, Hartwig JF. Angew. Chem. Int. Ed. 2008; 47: 2127
    • 19f Martín R, Buchwald SL. Angew. Chem. Int. Ed. 2007; 46: 7236
    • 19g Martín R, Buchwald SL. Org. Lett. 2008; 10: 4561
  • 20 García-Fortanet J, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 8108
  • 21 Nareddy P, Mantilli L, Guénée L, Mazet C. Angew. Chem. Int. Ed. 2012; 51: 3826
    • 22a Roy AH, Hartwig JF. J. Am Chem. Soc. 2001; 123: 1232
    • 22b Roy AH, Hartwig JF. J. Am. Chem. Soc. 2003; 125: 13944
  • 23 Newman SG, Lautens M. J. Am. Chem. Soc. 2010; 132: 11416