Subscribe to RSS
DOI: 10.1055/s-0028-1083255
Organocatalytic Domino Michael-Aldol Reaction of Ketones and α,β-Unsaturated Trifluoromethyl Ketones
Publication History
Publication Date:
01 December 2008 (online)

Abstract
Pyrrolidine-catalyzed domino Michael-aldol reaction of α,β-unsaturated trifluoromethyl ketones and ketones was achieved under mild conditions; β-hydroxy-β-trifluoromethyl cyclohexanones were obtained in high yields with good diastereoselectivities.
Key words
bicyclic compounds - cyclizations - domino reactions - organocatalytic - trifluoromethyl
-
1a
Banks RE.Smart BE.Tatlow JC. Organofluorine Chemistry, Principle, and Commercial Applications Plenum Press; New York: 1994. -
1b
Hiyama T. Organofluorine Compounds, Chemistry and Application Springer; Berlin: 2000. -
1c
Filler R.Kobayashi Y.Yagupolskii LM. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications Elsevier; Amsterdam: 1993. -
1d
Ojima I.McCarthy JR.Welch JT. Biomedical Frontiers of Fluorine Chemistry American Chemical Society; Washington DC: 1996. -
2a
Mikami K. In Asymmetric Fluoroorganic Chemistry: Synthesis, Application and Future DirectionsRamachandran PV. American Chemical Society; Washington DC: 1999. p.255-269 -
2b
Ren J.Milton J.Weaver KL.Short SA.Stuart DI.Stammers DK. Structure 2000, 8: 1089 -
2c
Pedersen OS.Pedersen EB. Synthesis 2000, 479 - 3
Lin P.Jiang J. Tetrahedron 2000, 56: 3635 -
4a
Prakash GKS.Hu J. In Fluorine-Containing SynthonsSoloshonok VA. American Chemical Society; Washington DC: 2005. p.16-56 -
4b
Langlois BR.Billard T. In Fluorine-Containing SynthonsSoloshonok VA. American Chemical Society; Washington DC: 2005. p.57-86 - For reviews on enantiomeric synthesis of trifluoromethyl tertiary alcohols by trifluoromethylation reaction, see:
-
4c
Ma J.-A.Cahard D. Chem. Rev. 2004, 104: 6119 -
4d
Billard T.Langlois BR. Eur. J. Org. Chem. 2007, 891 -
5a
Sosnovskikh VY.Ovsyannikov IS.Aleksandrova IA. J. Org. Chem. USSR (Engl. Transl.) 1992, 28: 420 -
5b
Soloshonok VA.Avilov DV.Kukhar VP. Tetrahedron 1996, 52: 12433 -
5c
Soloshonok VA.Kacharov AD.Avilov DV.Ishikawa K.Nagashima N.Hayashi T. J. Org. Chem. 1997, 62: 3470 -
5d
Funabiki K.Isomura A.Yamaguchi Y.Hashimoto W.Matsunaga K.Shibata K.Matsui M. J. Chem. Soc., Perkin Trans. 1 2001, 2578 -
5e
Barten JA.Funabiki K.Roschenthaler GV. J. Fluorine Chem. 2002, 113: 105 - For enantiomeric synthesis of trifluoromethyl tertiary alcohols from trifluoromethyl ketones, see:
-
5f
Pierce ME.Parsons RL.Radesca LA.Lo YS.Silverman S.Moore JR.Islam Q.Choudhury A.Fortunak JMD.Nguyen D.Morgan C.Luo SJ.Davis WP.Confalone PN.Chen C.-Y.Tillyer RD.Frey L.Tan L.Xu F.Zhao D.Thompson AS.Corley EG.Grabowski EJJ.Reamer R.Reider PJ. J. Org. Chem. 1998, 63: 8536 -
5g
Török B.Abid M.London G.Esquibel J.Török M.Mhadgut SC.Yan P.Prakash GKS. Angew. Chem. Int. Ed. 2005, 44: 3086 -
6a
List B.Lerner RA.Barbas CF. J. Am. Chem. Soc. 2000, 122: 2395 -
6b
Notz W.List B. J. Am. Chem. Soc. 2000, 122: 7386 -
6c
List B.Pojarliev P.Castello C. Org. Lett. 2001, 3: 573 -
6d
Sakthivel K.Notz W.Bui T.Barbas CF. J. Am. Chem. Soc. 2001, 123: 5260 -
6e
Pidathala C.Hoang L.Vignola N.List B. Angew. Chem. Int. Ed. 2003, 42: 2785 ; Angew. Chem. 2003, 115, 2891 - For reviews, see:
-
6f
List B. Synlett 2001, 1675 -
6g
List B. Tetrahedron 2002, 58: 5573 -
6h
List B. Acc. Chem. Res. 2004, 37: 548 -
6i
Notz W.Tanaka F.Barbas CF. Acc. Chem. Res. 2004, 37: 580 -
7a
Qiu L.Shen Z.Shi C.Liu Y.Zhang Y. Chin. J. Chem. 2005, 23: 584 -
7b
Wang X.-J.Zhao Y.Liu J.-T. Org. Lett. 2007, 9: 1343 -
8a
Tordeux M.Wakselman C. Synth. Commun. 1991, 21: 1243 -
8b
Burgart YV.Forkin AS.Bazyl’ IT.Saloutin VL. Russ. Chem. Bull. 1997, 46: 952 -
8c
Andrew RJ.Mellor JM.Reid G. Tetrahedron 2000, 56: 7255 -
8d
Nenajdenko VG.Druzhinin SV.Balenkova ES. Russ. Chem. Bull. 2004, 53: 435 - For organocatalytic domino Michael-aldol reactions, see:
-
9a
Eder U.Sauer G.Wiechert R. Angew. Chem., Int. Ed. Engl. 1971, 10: 496 -
9b
Hajos ZG.Parrish DR. J. Org. Chem. 1974, 39: 1615 -
9c
Kaneko S.Yoshino T.Katoh T.Terashima S. Tetrahedron 1998, 54: 5471 -
9d
Halland N.Aburel PS.Jørgensen KA. Angew. Chem. Int. Ed. 2004, 43: 1272 -
9e
Pukkinen J.Aburel PS.Halland N.Jørgensen KA. Adv. Synth. Catal. 2004, 346: 1077 -
9f
Gryko D. Tetrahedron: Asymmetry 2005, 16: 1377 -
9g
Marigo M.Bertelsen S.Landa A.Jørgensen KA. J. Am. Chem. Soc. 2006, 128: 5475 -
9h
Cao C.-J.Sun X.-L.Kang Y.-B.Tang Y. Org. Lett. 2007, 9: 4151 - For sulfa-Michael-aldol reaction, see:
-
9i
Wang W.Li H.Wang J.Zu L. J. Am. Chem. Soc. 2006, 128: 10354 - For oxa-Michael-aldol reaction, see:
-
9j
Govender T.Hojabri L.Maghaddam FM.Advidsson PI. Tetrahedron: Asymmetry 2006, 17: 1763 -
9k
Li H.Wang J.Timiyin E.-N.Zu L.Jiang W.Wei S.Wang W. Chem. Commun. 2007, 507 -
9l
Sunden H.Ibrahem I.Zhao G.-L.Eriksson L.Cordova A. Chem. Eur. J. 2007, 13: 574 - 11
Wang J.Li H.Zu L.Wang W. Adv. Synth. Catal. 2006, 348: 425 -
12a
Torri H.Nakadai M.Ishihara K.Saito S.Yamamoto H. Angew. Chem. Int. Ed. 2004, 43: 1983 -
12b
Tang Z.Yang Z.-H.Chen X.-H.Cun L.-F.Mi A.-Q.Jiang Y.-Z.Gong L.-Z. J. Am. Chem. Soc. 2005, 127: 9285 -
12c
Betancort JM.Sakthivel K.Thayumanavan R.Tanaka F.Barbas CF. Synthesis 2004, 1509 -
12d
Mase N.Watanabe K.Yoda H.Takabe K.Tanaka F.Barbas CF. J. Am. Chem. Soc. 2006, 128: 4966 -
12e
Cheng C.Sun J.Wang C.Zhang Y.Wei S.Jiang F.Wu Y. Chem. Commun. 2006, 215
Reference
Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 619907 (2a), CCDC 665816 (2m) and CCDC 665817 (2r). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].