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Synlett 2009(2): 320-327
DOI: 10.1055/s-0028-1087673
DOI: 10.1055/s-0028-1087673
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© Georg Thieme Verlag
Stuttgart ˙ New York
Catalytic Enantioselective α-Arylation of Carbonyl Compounds
Further Information
Received
21 July 2008
Publication Date:
15 January 2009 (online)
Publication History
Publication Date:
15 January 2009 (online)
Abstract
Enantioselective creation of benzylic quaternary centers still is a continuous challenge to many synthetic organic chemists. Among the existing methods for installation of this type of center, the direct asymmetric α-arylation of carbonyl compounds is very attractive due to the ready availability of the coupling substrates. Herein, we present some new tools to the catalytic asymmetric α-arylation of carbonyl compounds that overcame many of the drawbacks posted in previous methods for this type of reaction.
Key words
enolates - α-arylation - carbonyl compounds - palladium - nickel - quaternary benzylic centers
- For some publications in the creation of quaternary centers, see:
-
1a
Fuji K. Chem. Rev. 1993, 93: 2037 -
1b
Corey EJ.Guzman-Perez A. Angew. Chem. Int. Ed. 1998, 37: 388 -
1c
Christoffers J.Mann A. Angew. Chem. Int. Ed. 2001, 40: 4591 -
1d
Hayashi T.Yamasaki K. Chem. Rev. 2003, 103: 2829 -
1e
Douglas CJ.Overman LE. Proc. Natl. Acad. Sci. U. S. A. 2004, 101: 5363 -
1f
Shibasaki M.Kanai M.Matsunaga S. Aldrichimica Acta 2006, 39: 31 -
2a
Buncel E.Dust JM.Terrier F. Chem. Rev. 1995, 95: 2261 -
2b
Selvakumar N.Yadi Reddy B.Sunil Kumar G.Iqbal J. Tetrahedron Lett. 2001, 42: 8398 -
2c
Snow RJ.Butz T.Hammach A.Kapadia S.Morowick TM.Prokopowicz AS.Takahashi H.Tan JD.Tschantz MA.Wang X.-J. Tetrahedron 2002, 43: 7553 -
2d
Lawrence NJ.Davies CA.Gray M. Org. Lett. 2004, 26: 4957 -
2e
Bella M.Gobbelgaard S.Jorgensen KA. J. Am. Chem. Soc. 2005, 127: 3671 - 3
Culkin DA.Hartwig JF. Acc. Chem. Res. 2003, 36: 234 - 4
Palucki M.Buchwald SL. J. Am. Chem. Soc. 1997, 119: 11108 - 5
Hamann BC.Hartwig JF. J. Am. Chem. Soc. 1997, 119: 12382 - 6
Satoh T.Kawamura Y.Miura M.Nomura M. Angew. Chem., Int. Ed. Engl. 1997, 36: 1740 - 7
Åhman J.Wolfe JP.Troutman MV.Palucki M.Buchwald SL. J. Am. Chem. Soc. 1998, 120: 1918 - 8
Lee S.Hartwig JF. J. Org. Chem. 2001, 66: 3402 - 9
Arao T.Kondo K.Aoyama T. Chem. Pharm. Bull. 2006, 54: 1743 - 10
Hamada T.Chieffi A.Åhman J.Buchwald SL. J. Am. Chem. Soc. 2002, 124: 1261 - 11
Spielvogel DJ.Buchwald SL. J. Am. Chem. Soc. 2002, 124: 3500 - 12
Chen G.Kwong FY.Chan HO.Yu W.-Y.Chan ASC. Chem. Commun. 2006, 1413 - 13
Xie X.Chen Y.Ma D. J. Am. Chem. Soc. 2006, 128: 16050 -
14a
Kündig PE.Seidel TM.Jia H.Bernardinelli G. Angew. Chem. Int. Ed. 2007, 46: 8484 -
14b
Jia Y.Hillgren JM.Watson ML.Marsden SP.Kündig PE. Chem. Commun. 2008, 4040 - 15
Liao X.Weng Z.Hartwig JF. J. Am. Chem. Soc. 2008, 130: 195 - 16
Dalko PI. Enantioselective Organocatalysis Wiley-VCH; Weinheim: 2007. - 17
Alemán J.Cabrera S.Maerten E.Overgaard J.Jørgensen KA. Angew. Chem. Int. Ed. 2007, 46: 5520 - 18
Alemán J.Richter B.Jørgensen KA. Angew. Chem. Int. Ed. 2007, 46: 5515 - 19
Aggarwal VK.Olofsson B. Angew. Chem. Int. Ed. 2005, 44: 5516 - 20
García-Fortanet J.Buchwald SL. Angew. Chem. Int. Ed. 2008, 47: 8108