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-00000083.xml
Synlett 2003(3): 0408-0410
DOI: 10.1055/s-2003-37120
DOI: 10.1055/s-2003-37120
LETTER
© Georg Thieme Verlag Stuttgart · New York
Ruthenium-Bisimine: A New Catalytic Precursor for Regioselective Allylic Alkylation
Further Information
Received
6 December 2003
Publication Date:
07 February 2003 (online)
Publication History
Publication Date:
07 February 2003 (online)
![](https://www.thieme-connect.de/media/synlett/200303/lookinside/thumbnails/10.1055-s-2003-37120-1.jpg)
Abstract
New complexes [Cp*Ru(bisimine)Cl] are active catalysts for the regioselective alkylation of allylic carbonates by soft carbonucleophiles, in favour of the branched isomers. The catalysts can be conveniently prepared in situ from [Cp*Ru(cod)Cl] and a bulky aromatic bisimine.
Keywords
regioselective allylic alkylation - ruthenium(bisimine) complex catalysed - coupling reactions
-
1a
Trost BM.van Vranken DL. Chem. Rev. 1996, 96: 395 -
1b
Pfaltz A.Lautens M. In Comprehensive Asymmetric CatalysisJacobsen EN.Pfaltz A.Yamamoto H. Springer; Berlin: 1999. p.833 -
1c
Johansen M.Jorgenssen KA. Chem. Rev. 1998, 98: 1689 -
1d
Tsuji J. In Transition Metal Reagents and Catalysts. Innovations in Organic Synthesis Wiley; Chichester: 2000. p.109 -
2a
Trost BM. Acc. Chem. Res. 1996, 29: 355 -
2b
Kudis S.Helmchen G. Angew. Chem. Int. Ed. 1998, 37: 3047 -
2c
Pfaltz A.Helmchen G. Acc. Chem. Res. 2000, 33: 336 -
3a
Goux C.Massacret M.Lhoste P.Sinou D. Organometallics 1995, 14: 4585 -
3b
Trost BM.Toste FD. J. Am. Chem. Soc. 1998, 120: 9074 -
3c
Blacker AJ.Clarke ML.Loft MS.Williams JMJ. Org. Lett. 1999, 1: 1969 -
3d
Hayashi T.Kawatsura M.Uozumi Y. J. Am. Chem. Soc. 1998, 120: 1681 -
4a
Trost BM.Tometzki GB.Hung MH. J. Am. Chem. Soc. 1987, 109: 2176 -
4b
Lloyd-Jones GC.Pfaltz A. Angew. Chem., Int. Ed. Engl. 1995, 34: 462 -
4c
Trost BM.Dogra K.Hachiya I.Emura T.Hughes DL.Krska S.Reamer RA.Palucki M.Yasuda N.Reider PJ. Angew. Chem. Int. Ed. 2002, 41: 1929 -
4d
Takeuchi R.Ue N.Tanabe K.Yamashita K.Shiga N. J. Am. Chem. Soc. 2001, 123: 9525 -
4e
Bartels B.Helmchen G. Chem. Commun. 1999, 741 -
4f
Evans PA.Kennedy LJ. J. Am. Chem. Soc. 2001, 123: 1234 -
4g
Blacker AJ.Clarke ML.Loft MS.Williams JMJ. Chem. Commun. 1999, 913 -
4h
Kurosawa H. J. Chem. Soc., Dalton Trans. 1979, 939 -
4i
Brown JM.MacIntyre JE. J. Chem. Soc., Perkin Trans. 2 1985, 961 -
5a
Minami I.Shimizu I.Tsuji J. J. Organomet. Chem. 1985, 296: 269 -
5b
Zhang SW.Mitsudo T.Kondo T.Watanabe Y. J. Organomet. Chem. 1993, 450: 197 -
5c
Zhang SW.Mitsudo T.Kondo T.Watanabe Y. J. Organomet Chem. 1995, 485: 55 -
5d
Kondo T.Ono H.Satabe N.Mitsudo T.Watanabe Y. Organometallics 1995, 14: 1945 -
5e
Trost BM.Fraisse PL.Ball ZT. Angew. Chem. Int. Ed. 2002, 41: 1059 -
5f
Kang S.-K.Kim D.-Y.Hong R.-K.Ho P.-S. Synth. Commun. 1996, 26: 3225 -
5g
Matsushima Y.Onitsuka K.Kondo T.Mitsudo T.Takahashi SJ. J. Am. Chem. Soc. 2001, 123: 10405 -
6a
Le Paih J.Dérien S.Özdemir I.Dixneuf PH. J. Am. Chem. Soc. 2000, 122: 7400 -
6b
Le Paih J.Dérien S.Bruneau C.Demerseman B.Toupet L.Dixneuf PH. Angew. Chem. Int. Ed. 2001, 40: 2912 -
6c
Le Paih J.Dérien S.Dixneuf PH. Chem. Commun. 1999, 1437 - 7
Tsuji J.Minami I. Acc. Chem. Res. 1987, 20: 140
References
(C5Me5)RuCl(MesN=CH-CH=NMes): selected 1H NMR data (200 MHz): δ (ppm) 1.07 (s, 15 H, C5Me5), 1.87 (s, 6 H, 2 Me), 2.30 (s, 6 H, 2 Me), 2.38 (s, 6 H, 2 Me), 6.82 (s, 2 H, 2 HAr), 6.92 (s, 2 H, 2 HAr), 8.68 (s, 2 H, 2 CH=N).