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Synlett 2012(1): 1-5
DOI: 10.1055/s-0031-1290111
DOI: 10.1055/s-0031-1290111
SYNPACTS
© Georg Thieme Verlag
Stuttgart ˙ New York
Recent Developments in Asymmetric Coupling of Enolates
Further Information
Received
29 October 2011
Publication Date:
13 December 2011 (online)
Publication History
Publication Date:
13 December 2011 (online)
Abstract
Recent progress in transition-metal-catalyzed, asymmetric couplings of carbonyl compounds is summarized. Particular emphasis is placed on the intermolecular processes that form tertiary stereocenters, which was a challenging problem for many years.
Key words
cross-coupling - arylation - palladium - copper - enolates
- 1
Semmelhack MF.Stauffer RD.Rogerson TD. Tetrahedron Lett. 1973, 14: 4519 -
2a
Palucki M.Buchwald SL. J. Am. Chem. Soc. 1997, 119: 11108 -
2b
Hamann BC.Hartwig JF. J. Am. Chem. Soc. 1997, 119: 12382 -
2c
Satoh T.Kawamura Y.Miura M.Nomura M. Angew. Chem. Int. Ed. 1997, 36: 1740 - 3
Landoni MF.Soraci A. Curr. Drug Metab. 2001, 2 37 - 4
Harrington PJ.Lodewijk E. Org. Process Res. Dev. 1997, 1: 72 - Reviews:
-
5a
Bellina F.Rossi R. Chem. Rev. 2010, 110: 1082 -
5b
Johansson CCC.Colacot TJ. Angew. Chem. Int. Ed. 2010, 49: 676 -
5c
Burtoloso ACB. Synlett 2009, 320 - 6
Huang Z.Liu Z.Zhou J. J. Am. Chem. Soc. 2011, 133: 15882 - 7
Allen AE.MacMillan DWC. J. Am. Chem. Soc. 2011, 133: 4260 - 8
Harvey JS.Simonovich SP.Jamison CR.MacMillan DWC. J. Am. Chem. Soc. 2011, 133: 13782 - 9
Bigot A.Williamson AE.Gaunt MJ. J. Am. Chem. Soc. 2011, 133: 13778 - 10 A review on Ni-catalyzed, asymmetric
couplings of α-halocarbonyl compounds:
Glorius F. Angew. Chem. Int. Ed. 2008, 47: 8347 -
11a
Liao X.Weng Z.Hartwig JF. J. Am. Chem. Soc. 2008, 130: 195 -
11b
Hamada T.Chieffi A.Åhman J.Buchwald SL. J. Am. Chem. Soc. 2002, 124: 1261 -
11c
Ge S.Hartwig JF. J. Am. Chem. Soc. 2011, 133: 16330 - 12
Spielvogel DJ.Buchwald SL. J. Am. Chem. Soc. 2002, 124: 3500 - Examples of arylations of amides:
-
13a
Taylor AM.Altman RA.Buchwald SL. J. Am. Chem. Soc. 2009, 131: 9900 -
13b
Lee S.Hartwig JF. J. Org. Chem. 2001, 66: 3402 - 14
García-Fortanet J.Buchwald SL. Angew. Chem. Int. Ed. 2008, 47: 8108 - 15 Asymmetric coupling of aryl bromides
and one silyl ketene acetal was reported to give moderate ee:
Galarini R.Musco A.Pontellini R.Santi R. J. Mol. Catal. 1992, 72: L11 - 16
Liu X.Hartwig JF. : J. Am. Chem. Soc. 2004, 126: 5182 - 17
Carfagna C.Musco A.Sallese G.Santi R.Fiorani T.
J. Org. Chem. 1991, 56: 261 - 18 Copper-catalyzed enantioselective
arylation of 2-methyl acetoacetates:
Xie X.Chen Y.Ma D. J. Am. Chem. Soc. 2006, 128: 16050 - Intramolecular, asymmetric arylation of aldehydes:
-
19a
Um JM.Gutierrez O.Schoenebeck F.Houk KN.MacMillan DWC. J. Am. Chem. Soc. 2010, 132: 6001 -
19b
Conrad JC.Kong J.Laforteza BN.MacMillan DWC. J. Am. Chem. Soc. 2009, 131: 11640