Synlett, Table of Contents LETTER © Georg Thieme Verlag Stuttgart · New York Dipeptide-Catalyzed Direct Asymmetric Aldol Reaction Lan-Xiang Shi, Qi Sun, Ze-Mei Ge, Yong-Qiang Zhu, Tie-Ming Cheng, Run-Tao Li*School of Pharmaceutical Sciences, Peking University, Beijing 100083, P. R. ChinaFax: +86(10)62346154; e-Mail: Lirt@mail.bjmu.edu.cn; Recommend Article Abstract Buy Article All articles of this category 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 Full Text References References 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
