RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2008(2): 161-184
DOI: 10.1055/s-2007-1000848
DOI: 10.1055/s-2007-1000848
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Reaction of Linear Push-Pull Enamines at the β′-Position
Weitere Informationen
Received
30 July 2007
Publikationsdatum:
18. Dezember 2007 (online)
Publikationsverlauf
Publikationsdatum:
18. Dezember 2007 (online)
Abstract
Enamine tautomerism is often the main cause of regioselectivity problems in the chemistry of enamines derived from ketones. Linear push-pull tertiary enamines featuring a methyl (methylene) group at the α-position do not experience such tautomerism; nevertheless, a number of reactions proceed with participation of the methyl (methylene) group. It was our objective to analyze all known reactions of this type and show their high synthetic potential.
1 Introduction
2 Electrophilic Functionalization of Preformed Lithiated or Silylated Enamines
3 Uncatalyzed Reactions of Monoelectrophilic Reagents at the Methyl (Methylene) Group
4 Reactions Proceeding at Both the β- and β′-Carbon of the Enamine
5 Reactions Proceeding at the α-Methyl (Methylene) Group and β-Functional Group
6 Conclusion
Key words
push-pull enamines - electrophilic functionalizations - cyclization - 1,3-binucleophiles
-
1a
The Chemistry of Enamines
Rappoport Z. Wiley; Chichester: 1994. -
1b
Enamines: Synthesis, Structure and Reactions
Cook AG. Marcel Dekker; New York: 1988. - 9
Schlessinger RH.Poss MA. J. Am. Chem. Soc. 1982, 104: 357 - 13
Schlessinger RH.Poss MA.Richardson S. J. Am. Chem. Soc. 1986, 108: 3112 - 14
Schlessinger RH.Li Y.-J. J. Am. Chem. Soc. 1996, 118: 3301 - 18
Schlessinger RH.Gillman KW. Tetrahedron Lett. 1996, 37: 1331 - 19
Schlessinger RH.Gillman KW. Tetrahedron Lett. 1999, 40: 1257 - 2
Yoshimoto M.Ishida N.Hiraoka T. Tetrahedron Lett. 1973, 39 - 3
Chan TH.Kang GJ. Tetrahedron Lett. 1982, 23: 3011 - 4
Kang GJ.Chan TH. Can. J. Chem. 1985, 63: 3102 - 5
Dugger RW.Heathcock CH. J. Org. Chem. 1980, 45: 1181 - 6
Williard PG.Tata JR.Schlessinger RH.Adams AD.Iwanowicz EJ. J. Am. Chem. Soc. 1988, 110: 7901 - 7
Adams AD.Schlessinger RH.Tata JA.Venit JJ. J. Org. Chem. 1986, 51: 3068 -
8a
Cram DJ.Elhafez FG. J. Am. Chem. Soc. 1952, 74: 5828 -
8b
Cram DJ.Wilson DR. J. Am. Chem. Soc. 1963, 85: 1245 - 10
Schlessinger RH.Iwanowicz EJ.Springer JP. J. Org. Chem. 1986, 51: 3070 - 11
Fray MJ.Thomas EJ. J. Chem. Soc., Perkin Trans. 1 1985, 2763 - 12
Schlessinger RH.Bebernitz GR.Lin P. J. Am. Chem. Soc. 1985, 107: 1777 - 15
Dankwardt JW.Dankwardt SM.Schlessinger RH. Tetrahedron Lett. 1998, 39: 4983 - 16
Whitesell JK.Minton MA.Chen K.-M. J. Org. Chem. 1988, 53: 5383 - 17
Schlessinger RH.Li Y.-J.Von Langen DJ. J. Org. Chem. 1996, 61: 3226 - 20
Schlessinger RH.Pettus LH. J. Org. Chem. 1998, 63: 9089 - 21
Schlessinger RH.Tata JR.Springer JP. Tetrahedron Lett. 1987, 28: 5423 - 22
Schlessinger RH.Tata JR.Springer JP. J. Org. Chem. 1987, 52: 708 - 23
Schlessinger RH.Lin P.Poss M. Heterocycles 1987, 25: 315 - 24
Li Y.-J.Liu Z.-T.Yang S.-C. Tetrahedron Lett. 2001, 42: 8011 - 25
Lyubchanskaya VM.Muhanova TI.Alekseeva LM.Granik VG. Khim.-Farm. Zh. 1995, 29: 37 - 26
Vereshchagin LI.Gavrilov LD.Bolshedvorskaya RL.Kirillova LP.Ohapkina LL. Zh. Org. Khim. 1973, 9: 506 - 27
Satyanarayana J.Reddy KR.Ila H.Janjappa H. Tetrahedron Lett. 1992, 33: 6173 - 28
Reddy KR.Ila H.Janjappa H. Synthesis 1995, 929 - 29
Gravel D.Labelle M. Can. J. Chem. 1985, 63: 1874 - 30
Greaves PM.Landor SR. Chem. Commun. 1966, 322 - 31
Fomum ZT.Greaves PM.Landor PD.Landor SR. J. Chem. Soc., Perkin Trans. 1 1973, 1108 - 32
Bestmann HJ.Graf G.Hartung H.Kolewa S.Vilsmaier E. Chem. Ber. 1970, 103: 2794 - 33
Yoshimoto M.Hiraoka T.Kishida Y. Chem. Pharm. Bull. 1970, 18: 2469 - 34
Boehme H.Willinger G. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1969, 974 - 35
Volochnyuk DM.Kostyuk AN.Sibgatulin DA.Petrenko AE. Synthesis 2004, 2545 - 36
Sibgatulin DA.Volochnyuk DM.Kostyuk AN. Synlett 2005, 1904 - 37
Sibgatulin DA.Volochnyuk DM.Kostyuk AN. Tetrahedron Lett. 2007, 48: 2775 -
38a
Volochnyuk, D. M.; Kostyuk, A. N.; Sibgatulin, D. A.; Vovk, M. V.; Tolmachev, A. A.; Pinchuk, A. M. Abstracts of Papers, 14th European Symposium on Fluorine Chemistry, Poznan, Poland, July 11-16, 2004; Abstract AO-04.
-
38b
Sibgatulin, D. A.; Volochnyuk, D. M.; Kostyuk, A. N. Abstracts of Papers, 7th All-Russian Conference, Fluorine Chemistry, Moscow, Russian Federation, June 5-9, 2006; Abstract P-45.
- 39
Moehrle H.Reinhardt HW. Arch. Pharm. (Weinheim Ger.) 1984, 317: 1017 - 40
Moehrle H.Reinhardt HW. Arch. Pharm. (Weinheim Ger.) 1984, 317: 156 - 41
Sibgatulin DA.Volochnyuk DM.Rusanov EB.Kostyuk AN. Synthesis 2006, 1625 - 42
Burger K.Hein F. Liebigs Ann. Chem. 1982, 853 - 43
Boehme H.Traenka M. Liebigs Ann. Chem. 1985, 149 - 44
Alt GH.Speziale AJ. J. Org. Chem. 1964, 29: 798 - 45
Alt GH.Speziale AJ. J. Org. Chem. 1964, 29: 795 - 46
Helmers R. Tetrahedron Lett. 1966, 1905 - 47
Jacquier R.Maurey G. Bull. Soc. Chim. Fr. 1967, 320 - 48
Kostyuk AN.Svyaschenko YV.Volochnyuk DM.Lysenko NV.Tolmachev AA.Pinchuk AM. Tetrahedron Lett. 2003, 6487 - 49
Van den Goorberg JAM.Van der Gen A. Tetrahedron Lett. 1980, 21: 3621 - 50
Woodward RB.Pachter IJ.Scheinbaum ML. J. Org. Chem. 1971, 36: 1137 - 51
Woodward RE, andBickel H. inventors; US Patent 4550162. - 52
Lauer WM.Cromwell NH. J. Am. Chem. Soc. 1942, 64: 612 - 53
Rao RB.Sing UP.Bhide GV. Tetrahedron Lett. 1967, 719 - 54
Tsuge O.Inaba A. Bull. Chem. Soc. Jpn. 1973, 46: 286 - 55
Simunek P.Bertolasi V.Lycka A.Machacek V. Org. Biomol. Chem. 2003, 1: 3250 - 56
Granik VG.Grizik SI.Solov’eva NP.Anisimova OS.Sheiker YuN. Russ. J. Org. Chem. (Engl. Transl.) 1984, 20: 673 - 57
Camps P.Jaime C.Molas J. Tetrahedron Lett. 1981, 22: 2487 - 58
Node M.Fujiwara T.Ichihashi S.Nishide K. Tetrahedron Lett. 1998, 39: 6331 - 59
Auricchio S.Bernardi R.Ricca A. Tetrahedron Lett. 1976, 4831 - 60
Boehme H.Traenka M. Liebigs Ann. Chem. 1985, 485 - 61
Kashima C.Yamamoto Y. J. Heterocycl. Chem. 1980, 17: 1141 - 62
Boehme H.Graetzel von Graetz J.Martin F.Matusch R.Nehne J. Liebigs Ann. Chem. 1980, 394 -
63a
Harris RLN.Huppatz JL.Phillips JN. Angew. Chem. 1976, 88: 539 -
63b
Harris RLN.Huppatz JL.Phillips JN. Aust. J. Chem. 1977, 30: 2213 - 64
Volochnyuk DM.Kostyuk AN.Sibgatulin DA.Chernega AN. Tetrahedron 2005, 61: 2839 - 65
Volochnyuk DM.Kostyuk AN.Sibgatulin DA.Chernega AN.Pinchuk AM.Tolmachev AA. Tetrahedron 2004, 60: 2361 - 66
Chkanikov ND. In Enamines in Organic Synthesis (in Russian) UO RAN; Ekaterenburg: 2001. p.108-120 - 67
Hickmott PW.Sheppard G. J. Chem. Soc., Perkin Trans. 1 1972, 1038 - 68
Belyaeva OY.Granik VG.Glushkov RG.Vlasova TF.Anisimova OS. Chem. Heterocycl. Compd. (Engl. Transl.) 1978, 14: 653 - 69
Lyubchanskaya VM.Sarisova LS.Alekseeva LM.Granik VG. Khim.-Farm. Zh. 1994, 49 - 70
Nitta H.Takimoto K.Ueda I. Chem. Pharm. Bull. 1992, 40: 858 - 71
Take K.Okumura K.Takimoto K.Kato M.Ohtsuka M.Shiokawa Y. Chem. Pharm. Bull. 1991, 39: 2915 - 72
Goerlitzer K.Trittmacher J.Jones PG.Frohberg P.Drutkowsi G. Pharmazie 2003, 58: 776 - 73
Michael JP.Howard AS.Katz RB.Zwane MI. Tetrahedron Lett. 1992, 4751 - 74
Singh H.Dolly Hundal MS.Hundal G.Singh P.Singh Chimni S.Kumar S. Tetrahedron 1998, 54: 7563 - 75
Tsuge O.Inaba A. Heterocycles 1975, 3: 1081 - 76
Tsuge O.Inaba A. Bull. Chem. Soc. Jpn. 1976, 49: 2828 - 77
Volochnyuk DM.Kostyuk AN.Bol’but AV.Sibgatulin DA.Kuklya AS.Vovk MV. Synthesis 2004, 2196 -
78a
Gromov SP.Yashunskii DV.Sagitullin RS.Bundel YuG. Dokl. Chem. (Engl. Transl.) 1987, 292: 12 -
78b
Gromov SP,Yashunskii DV,Sagitullin RS, andKost AN. inventors; SU Patent 1049484. ; Chem. Abstr. 1984, 100, 120898 - 79
Gompper R.Heinemann U. Angew. Chem. 1980, 92: 207 - 80
Kostyuk AN.Svyaschenko YV.Volochnyuk DM. Tetrahedron 2005, 61: 9263 - 81
Svyaschenko YV.Barnich BB.Kostyuk AN.Volochnyuk DM. Tetrahedron 2007, 63: 5656 - 82
Kostyuk AN.Svyaschenko YV.Volochnyuk DM. In Nitrogen-Containing Heterocycles Vol. 2:Kartsev VG. ICSPF Press; Moscow: 2006. p.322-323 - 83
Tsuge O.Inaba A. Bull. Chem. Soc. Jpn. 1973, 46: 2221 - 84
Burger K.Wassmuth U.Hein F.Rottegger S. Liebigs Ann. Chem. 1984, 991 -
85a
Akhrem AA.Chernov YuG. Synthesis 1980, 996 -
85b
Akhrem AA.Chernov YuG. Dokl. Chem. (Engl. Transl.) 1980, 255: 865 - 86
Holy A.Arnold Z. Collect. Czech. Chem. Commun. 1965, 53