Application

No.123
Chiral Methylenebis(oxazoline) Ligands
M1401 (+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] (1a) 500mg
M1402 (-)-2,2'-Methylenebis[(3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] (1b) 500mg

The chiral bidentate ligands 1 forms stable chiral metal complexes with Lewis acids such as Cu(ClO4)2·6H2O, Cu(OTf)2, and Ni(ClO4)2. These chiral metal complexes are Lewis acid catalysts that have excellent stereocontrol and are used in a number of assymmetric reactions. For example, the dienophiles 2 undergo a Diels-Alder reaction with cyclopentadiene in the presence of chiral metal complex derived from 1b and Cu(ClO4)2·6H2 to give the adducts 3 with high enantioselectivity.1b) Metal complexes of 1 are also effective chiral catalyst for asymmetric hetero-Diels-Alder reactions,2a) radical reactions,2b) sigmatropic rearrangements,2c) and phospho-transfer reaction.2d) The utility of ligand 1 is expected to increase as various substituents are introduced to methylene position of 1.3)

References

1) Diels-Alder catalysis with a bis(oxazoline) complex
a)I. W. Davies, L. Gerena, D. Cai, R. D. Larsen, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett., 38, 1145 (1997).
b)A. K. Ghosh, H. Cho, J. Cappiello, Tetrahedron: Asymmetry, 9, 3687 (1998).
2) Applications in catalytic reaction of bis(oxazoline) complexes
a)T. Saito, K. Takekawa, T. Takahashi, Chem. Commun., 1999, 1001.
b)N. A. Porter, H. Feng, I. K. Kavrakova, Tetrahedron Lett., 40, 6713 (1999).
c)X. Zhang, M. Ma, J. Wang, Tetrahedron: Asymmetry, 14, 891 (2003).
d)M. Jiang, S. Dalgarno, C. A. Kilner, M. A. Halcrow, T. P. Kee, Polyhedron, 20, 2151 (2001).
3) Enantioselective conjugate addition
a)D. M. Barnes, et al., J. Am. Chem. Soc., 124, 13097 (2002).

Related Compounds

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B2217 (R,R)-2,6-Bis(4-isopropyl-2-oxazolin-2-yl)pyridine 1g
250mg
B2218 (S,S)-2,6-Bis(4-isopropyl-2-oxazolin-2-yl)pyridine 500mg
B2219 (R,R)-2,6-Bis(4-phenyl-2-oxazolin-2-yl)pyridine 1g
250mg
B2220 (S,S)-2,6-Bis(4-phenyl-2-oxazolin-2-yl)pyridine 250mg
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I0567 (S,S)-(-)-2,2-Bis(4-tert-butyl-2-oxazolin-2-yl)propane 1g
100mg
D2823 (R,R)-2,2-Bis(4-phenyl-2-oxazolin-2-yl)propane 1g
250mg
I0582 (S,S)-2,2-Bis(4-phenyl-2-oxazolin-2-yl)propane 1g
250mg
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