Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2002(11): 1601-1606
DOI: 10.1055/s-2002-33345
DOI: 10.1055/s-2002-33345
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York
Substituted Pyridylamide
Ligands in Microwave-Accelerated
Mo(0)-Catalysed Allylic
Alkylations
Further Information
Received
21 May 2002
Publication Date:
23 August 2002 (online)
Publication History
Publication Date:
23 August 2002 (online)
Abstract
Novel 4- and 6-substituted bis-pyridylamides were prepared by microwave accelerated nucleophilic substitution of the 4- and 6-halo substituted derivatives of the parent ligand 1a. The ligands were used in the asymmetric allylation of cinnamyl carbonate catalysed by Mo(0) in which the 4-chloro- and 4-pyrrolidyl substituted ligand derivatives exhibited high regioselectivity (74:1 and 88:1, respectively) and enantioselectivity (96% ee), whereas 6-substituted ligands afforded no product under the same conditions. Other allylic substrates were used to explore the generality of the procedure.
Key words
molybdenum - allylations - asymmetric catalysis - pyridylamides - microwaves
-
1a
Faller JW.Chao K. H. J. Am. Chem. Soc. 1983, 105: 3893 -
1b
Trost BM.Lautens M. J. Am. Chem. Soc. 1982, 104: 5543 -
1c
Trost BM.Lautens M. J. Am. Chem. Soc. 1983, 105: 3344 -
2a
Trost BM.Hachiya I. J. Am. Chem. Soc. 1998, 120: 1104 -
2b
Trost BM.Hilbrand S.Dogra K. J. Am. Chem. Soc. 1999, 121: 10416 -
3a
Glorius F.Pfaltz A. Org. Lett. 1999, 1: 141 -
3b
Glorius F.Neuburger M.Pfaltz A. Helv. Chim. Acta 2001, 84: 3178 - 4
Malkov AV.Baxendale IR.Bella M.Langer V.Fawcett J.Rusell DR.Mansfield DJ.Valko M.KoË P. Organometallics 2001, 20: 673ovsk - 5
Malkov AV.Spoor P.Vinader V.KoË P. Tetrahedron Lett. 2001, 42: 509ovsk -
6a
Bremberg U.Larhed M.Moberg C.Hallberg A. J. Org. Chem. 1999, 64: 1082 -
6b
Kaiser N.-F.Bremberg U.Larhed M.Moberg C.Hallberg A. J. Organomet. Chem. 2000, 603: 2 -
6c
Bremberg U.Lutsenko S.Kaiser N.-F.Larhed M.Hallberg A.Moberg C. Synthesis 2000, 1004 -
6d
Lutsenko S.Moberg C. Tetrahedron: Asymmetry 2001, 12: 2529 - 7
Kaiser N.-F.Bremberg U.Larhed M.Moberg C.Hallberg A. Angew. Chem. Int. Ed. 2000, 39: 3596 -
8a
Adolfsson H.Moberg C. Tetrahedron: Asymmetry 1995, 6: 2023 -
8b
Moberg C.Adolfsson H.Wärnmark K. Acta Chem. Scand. 1996, 50: 195 - 9
Belda O.Kaiser N.-F.Bremberg U.Larhed M.Hallberg A.Moberg C. J. Org. Chem. 2000, 65: 5868 - 11
Joule M.Mills K. Heterocyclic Chemistry Blackwell Science; Oxford: 2000. - 12
Conlon DA.Yasuda N. Adv. Synth. Catal. 2001, 343: 137 - 13
Hughes DL.Palucki M.Yasuda N.Reamer RA.Reider PJ. J. Org. Chem. 2002, 67: 2762 - 14
Lehmann J.Lloyd-Jones GC. Tetrahedron 1995, 51: 8863 - 15
Sammakia T.Hurley TB. J. Org. Chem. 2000, 65: 974 - 16
You S.-L.Zhu X.-Z.Luo Y.-M.Hou X.-L.Dai L.-X. J. Am. Chem. Soc. 2001, 123: 7471
References
Belda, O.; Moberg, C., manuscript under preparation.