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DOI: 10.1055/s-2006-947357
Ruthenium-Catalyzed Enaminoketone Formation from Propargyl Alcohols
Publication History
Publication Date:
24 July 2006 (online)
Abstract
Monomeric ruthenium(0) complexes containing electronically coupled dienone ligands were found to catalyze the formation of enaminoketones from propargyl alcohols.
Key words
aminations - enaminoketones - homogenous catalysis - propargyl alcohols - ruthenium
-
1a
Shvo Y.Czarkie D. J. Am. Chem. Soc. 1986, 108: 7400 -
1b
Jung HM.Shin ST.Kim YH.Kim M.-J.Park J. Organometallics 2001, 20: 3370 -
1c
Jung HM.Choi JH.Lee SO.Kim YH.Park JH.Park J. Organometallics 2002, 21: 5674 - 2
Menashe N.Shvo Y. Organometallics 1991, 10: 3885 - 3
Shvo Y.Czarkie D. J. Organomet. Chem. 1986, 315: C25 -
4a
Almeida MLS.Beller M.Wang G.-Z.Bäckvall J.-E. Chem. Eur. J. 1996, 2: 1533 -
4b
Almeida MLS.Kocovsky P.Bäckvall J.-E. J. Org. Chem. 1996, 61: 6587 -
4c
Csjernyik G.Ell AH.Fadini L.Pugin B.Bäckvall J.-E. J. Org. Chem. 2002, 67: 1657 - 5
Ell AH.Samec JSM.Brasse C.Bäckvall J.-E. Chem. Commun. 2002, 1144 -
6a
Larsson ALE.Persson BA.Bäckvall J.-E. Angw. Chem., Int. Ed. Engl. 1997, 36: 1211 -
6b
Larsson ALE.Persson BA.Ray ML.Bäckvall J.-E. J. Am. Chem. Soc. 1999, 121: 1645 -
6c
Pamies O.Bäckvell J.-E. Chem. Rev. 2003, 103: 3247 - 7
Pamies O.Ell AH.Samec JSM.Hermanns N.Bäckvell J.-E. Tetrahedron Lett. 2002, 43: 4699 - 8
Choi JH.Kim N.Shin YJ.Park JH.Park J. Tetrahedron Lett. 2004, 45: 4607 -
9a
Blum Y.Shvo Y.Chodosh DF. Inorg. Chim. Acta 1985, 97: C25 -
9b
Blum Y.Shvo Y.Czarkie D.Rahamim Y. Organometallics 1985, 4: 1459 -
9c
Blum Y.Shvo Y. Isr. J. Chem. 1984, 24: 144
References and Notes
Characterization Data for Typical Enaminoketones.
Compound E-7c: C15H17NO3, yellow oil (rotamers 4:1). 1H NMR (300 MHz, CDCl3): δ = 1.90-2.34 (m, 4 H), 3.50-3.55 (m, 2 H), 3.75 (s, 3 H), 4.16 and 4.29 (t, J = 8.1 Hz, 1 H), 5.67 and 5.77 (d, J = 12.4 Hz, 1 H), 7.37-7.46 (m, 3 H), 7.87-8.01 (m, 3 H). 13C NMR (75 MHz, DEPT, CDCl3): δ = 23.2 and 25.1 (CH2), 27.5 and 29.7 (CH2), 45.1 and 46.0 (CH2), 52.5 (CH3), 60.4 and 60.9 (CH), 92.9 and 94.8 (CH), 127.4 and 127.5 (CH), 127.9 and 128.0 (CH), 130.6 and 131.0 (CH), 140.0 and 140.5 (C), 149.3 and 149.8 (CH), 166.3 and 172.1, 188.8 (C). IR: 3056, 3024, 2956, 2878, 1741, 1662, 1633, 1580, 1539, 1449, 1364, 1340, 1304, 1274, 1209, 1166, 1090, 1051, 1026, 1008, 991, 925, 893, 837, 758, 706, 621, 557 cm-1. MS (EI): m/z (%) = 259 (45) [M+], 200 (100), 172 (34), 154 (58), 105 (70), 77 (54), 70 (36). HRMS: m/z calcd: 259.12085; found: 259.12007.
Compound Z-7d: C12H13NO, yellow oil. 1H NMR (400 MHz, CDCl3): δ = 3.89 (tt, J = 5.6, 1.6 Hz, 2 H), 5.21 (dq, J = 10.2, 1.4 Hz, 1 H), 5.27 (dq, J = 17.1, 1.7 Hz, 1 H), 5.75 (d, J = 7.5 Hz, 1 H), 5.90 (ddt, J = 17.1, 10.3, 5.1 Hz, 1 H), 6.93 (dd, J = 12.8, 7.5 Hz, 1 H), 7.38-7.44 (m, 3 H), 7.88 (dd, J = 8.2, 1.4 Hz, 2 H), 10.3 (br s, NH). 13C NMR (100 MHz, DEPT, CDCl3): δ = 51.0 (CH2), 90.7 (CH), 117.1 (CH2), 127.0 (CH), 128.2 (CH), 130.9 (CH), 134.2 (CH), 139.7 (C), 154.0 (CH), 190.1 (C). IR: 3271, 3059, 3027, 2921, 2855, 1627, 1582, 1541, 1499, 1476, 1442, 1363, 1272, 1227, 1205, 1161, 1048, 1021, 988, 922, 867, 734, 699, 554 cm-1. MS (EI): m/z (%) = 187(58) [M+], 186 (39), 105 (100), 82 (89), 77 (55). HRMS: m/z calcd: 187.09972; found: 187.09941.