Asymmetric aldol reaction of 2-cyanopropionates catalysed by trans-chelating chiral diphosphine ligand TRAP–rhodium(I) complex
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Ryoichi Kuwano
Abstract
trans-Chelating chiral diphosphine TRAP ligands bearing P-aromatic groups are effective for RhI-catalysed asymmetric aldol reaction of 2-cyanopropionates with an aldehyde to give the corresponding aldol adduct with up to 93% ee.
References
For a review of catalytic asymmetric aldol reactions, see
M. Sawamura and
Y. Ito, in
Catalytic Asymmetric Synthesis, ed.
I. Ojima,
VCH,
New York,
1993,
p. 367 Search PubMed.
T. Naota, H. Taki, M. Mizuno and S.-I. Murahashi, J. Am. Chem. Soc., 1989, 111, 5954 CrossRefCAS; S.-I. Murahashi, T. Naota, H. Taki, M. Mizuno, H. Takaya, S. Komiya, Y. Mizuho, N. Oyasato, M. Hiraoka, M. Hirano and A. Fukuoka, J. Am. Chem. Soc., 1995, 117, 12 436 CrossRefCAS; S. Paganelli, A. Schionato and C. Botteghi, Tetrahedron Lett., 1991, 32, 2807 CrossRefCAS; H. Nemoto, Y. Kubota and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1994, 1665 RSC.
TRAP =(R,R)-2,2″-Bis[(S)-1-(dialkylphosphino)ethyl]-1,1″-biferrocene: M. Sawamura, H. Hamashima and Y. Ito, Tetrahedron: Asymmetry, 1991, 2, 593 Search PubMed; M. Sawamura, H. Hamashima, M. Sugawara, R. Kuwano and Y. Ito, Organometallics, 1995, 14, 4549 CrossRefCAS.
M. Sawamura, H. Hahashima and Y. Ito, J. Am. Chem. Soc., 1992, 114, 8295 CrossRefCAS; Tetrahedron,
1994,
50,
4439 Search PubMed; M. Sawamura, H. Hamashima, H. Shinoto and Y. Ito, Tetrahedron Lett., 1995, 36, 6479 Search PubMed.
K. Inagaki, K. Nozaki and H. Takaya, Synlett, 1997, 119 CAS.
Asymmetric allylic alkylation with TRAP–Rh–Pd catalyst system, see M. Sawamura, M. Sudoh and Y. Ito, J. Am. Chem. Soc., 1996, 118, 3309 Search PubMed.
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