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Synlett 2004(12): 2215-2217
DOI: 10.1055/s-2004-831324
DOI: 10.1055/s-2004-831324
LETTER
© Georg Thieme Verlag Stuttgart · New YorkDipeptide-Catalyzed Direct Asymmetric Aldol Reaction
Further Information
Received
18 June 2004
Publication Date:
31 August 2004 (online)
Publication History
Publication Date:
31 August 2004 (online)

Abstract
(l)-H-Pro-(l)-Phe-OH (4) were found to be efficient catalysts for direct asymmetric aldol reactions between acetone and various aldehydes. The reaction conditions use a DMSO-NMM-PEMG 5000 system at 0 °C in high yields (62-96%) and enantioselectivities (up to >99% ee).
Key words
aldol reaction - organocatalysis - enamine catalysis - dipeptides
- 1
List B.Lerner RA.Barbas CF. J. Am. Chem. Soc. 2000, 122: 2395 - For recent reviews, see:
- 2a
Gröger H.Wilken J. Angew. Chem. Int. Ed. 2001, 40: 529 - 2b
Dalko PI.Moisan L. Angew. Chem. Int. Ed. 2001, 40: 3726 - 2c
List B. Synlett 2001, 1675 - 2d
Jarvo ER.Miller SJ. Tetrahedron 2002, 58: 2481 - 2e
List B. Tetrahedron 2002, 58: 5573 - 2f
Alcaide B.Almendros P. Eur. J. Org. Chem. 2002, 1595 - 2g
Alcaide B.Almendros P. Angew. Chem. Int. Ed. 2003, 42: 858 - 3a
Notz W.List B. J. Am. Chem. Soc. 2000, 122: 7386 - 3b
List B.Pojarliev P.Castello C. Org. Lett. 2001, 3: 573 - 3c
Northrup AB.MacMillan DWC. J. Am. Chem. Soc. 2002, 124: 6798 - 3d
Hoang L.Bahmanyar S.Houk KN.List B. J. Am. Chem. Soc. 2003, 125: 16 - 3e
Pan QB.Zou BL.Wang YJ.Ma DW. Org. Lett. 2004, 6: 1009 - 4
Sakthivel K.Notz W.Bui T.Barbas CF. J. Am. Chem. Soc. 2001, 123: 5260 - 5
Tang Z.Jiang F.Yu LT.Cui X.Gong LZ.Mi AQ.Jiang YZ.Wu YD. J. Am. Chem. Soc. 2003, 125: 5262 - 6a
Martin HJ.List B. Synlett 2003, 1901 - 6b
Kofoed J.Nielsenb J.Reymonda JL. Bioorg. Med. Chem. Lett. 2003, 13: 2445 - 6c
Tang Z.Yang ZH.Cun LF.Gong LZ.Mi AQ.Jiang YZ. Org. Lett. 2004, 6: 2285 - 7a
Bahmanyar S.Houk KN.Martin HJ.List B. J. Am. Chem. Soc. 2003, 125: 2475 - 7b
Córdova A.Notz W.Barbas CF. J. Org. Chem. 2002, 67: 301 - 8
Dickerson TJ.Janda KD. J. Am. Chem. Soc. 2002, 124: 3220 - 9
Peng YY.Ding QP.Li ZC.Wang PG.Cheng JP. Tetrahedron Lett. 2003, 44: 3871 - 10
Mazur RH.Schlatter JH. J. Org. Chem. 1963, 28: 1025