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Synthesis 2010(15): 2577-2582
DOI: 10.1055/s-0029-1218815
DOI: 10.1055/s-0029-1218815
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkOne-Pot Approach for C-C Bond Formation through Ruthenium-Amido Complex Catalyzed Tandem Aldol Reaction/Hydrogenation
Weitere Informationen
Received
7 January 2010
Publikationsdatum:
15. Juni 2010 (online)
Publikationsverlauf
Publikationsdatum:
15. Juni 2010 (online)

Abstract
A one-pot novel and efficient approach was developed for the α-alkylation of various nitriles with carbonyl compounds using ruthenium-amido complex catalyst 1. The C-C bond was formed through aldol reaction followed by hydrogenation with triethylamine-formic acid (TEAF) and 1. Moderate to high yields were obtained, and a variety of functional groups were tolerated, including nitro and chloro groups, and a furan ring.
Key words
ruthenium-amido complex - tandem reaction - aldol reaction - hydrogenation - C-C bond
- Supporting Information for this article is available online:
- Supporting Information
- 1a
Brown HC.Midland MM.Levy AB. J. Am. Chem. Soc. 1972, 94: 3662MissingFormLabel - 1b
Kishimura K.Suzuki A.Dhillon RS. J. Org. Chem. 1990, 55: 6356MissingFormLabel - 1c
Jorgensen M.Iversen EH.Madsen R. J. Org. Chem. 2001, 66: 4625MissingFormLabel - 1d
List B.Castello C. Synlett 2001, 1687MissingFormLabel - 1e
Reid M.Rowe DJ.Taylor RJK. Chem. Commun. 2003, 18: 2284MissingFormLabel - 1f
Ramachary DB.Barbas CF. Chem. Eur. J. 2004, 10: 5323MissingFormLabel - 1g
Halland N.Aburel PS.Jorgensen KA. Angew. Chem. Int. Ed. 2004, 43: 1272MissingFormLabel - 2a
Goettmann F.Grosso D.Mercier F.Mathey F.Sanchez C. Chem. Commun. 2004, 1240MissingFormLabel - 2b
Dhevalapally BR.Kishor M.Ramakumar K. Tetrahedron Lett. 2005, 47: 651MissingFormLabel - 2c
Mubeen B.Asutosh VJ.Sudip M.Yoel S. Tetrahedron Lett. 2005, 46: 1885MissingFormLabel - 2d
Ken M.Noriaki F.Kohsuke M.Tomoo M.Kohki E.Kiyotomi K. Tetrahedron Lett. 2005, 46: 5507MissingFormLabel - 2e
Dhevalapally BR.Kishor M.Ramakumar K. Tetrahedron Lett. 2006, 47: 651MissingFormLabel - 3
Motokura K.Nishimura D.Mori K.Mizugaki T.Ebitani K.Kaneda K. J. Am. Chem. Soc. 2004, 126: 5662 - 4a
Pitta da Rocha I.Boucherle A.Luu DC. Eur. J. Med. Chem. 1974, 9: 462MissingFormLabel - 4b
Hartmann RW.Batzl C. J. Med. Chem. 1986, 29: 1362MissingFormLabel - 4c
Wu Z.-L.Li Z.-Y. J. Org. Chem. 2003, 68: 2479MissingFormLabel - 4d
Takaya H.Yoshida K.Isozaki K.Terai H.Murahashi SI. Angew. Chem. Int. Ed. 2003, 42: 3302MissingFormLabel - 5a
Hashiguchi S.Fujii A.Takehara J.Ikariya T.Noyori R. J. Am. Chem. Soc. 1995, 117: 7562MissingFormLabel - 5b
Haack KJ.Hashiguchi S.Fujii A.Ikariya T.Noyori R. Angew. Chem., Int. Ed. Engl. 1997, 36: 285MissingFormLabel - 5c
Noyori R.Hashiguchi S. Acc. Chem. Res. 1997, 30: 97MissingFormLabel - 5d
Noyori R.Yamakawa M.Hashiguchi S. J. Org. Chem. 2001, 66: 7931MissingFormLabel - 5e
Murata K.Konishi H.Ito M.Ikariya T. Organometallics 2002, 21: 253MissingFormLabel - 6a
Masahito W.Kunihiko M.Takao I. J. Am. Chem. Soc. 2003, 125: 7508MissingFormLabel - 6b
Masahito W.Ayako I.Hui W.Kunihiko M.Takao I. J. Am. Chem. Soc. 2004, 126: 11148MissingFormLabel - 6c
Yasuharu H.Masahito W.Ilya DG.Takao I. J. Am. Chem. Soc. 2008, 130: 2158MissingFormLabel - 7
Xue D.Chen Y.-C.Cui X.Wang Q.-W.Zhu J.Deng J.-G. J. Org. Chem. 2005, 70: 3584