Free accessResearch articleFirst published online 2012-3
Asymmetric 1,3-Dipolar Cycloaddition Reaction of C,N-Diphenylnitrone with Acryloyloxazolidinone Catalysed by Metal Complexes of Tridentate Bis(Oxazolinyl)Carbazole Ligand
Using a new type of Cu(OTf)2-bis(oxazolinyl)carbazole as the catalyst, 1,3-dipolar cycloaddition reactions between acryloyloxazolidinone and C,N-diphenylnitrone have been developed with 100% regioselectivity and an endo/exo ratio of 85:15 with a 94% ee of the endo-diastereomer.
KanoT., HashimotoT., MaruokaK., J. Am. Chem. Soc., 2005, 127, 11926.
8.
ZhuY.K., LiuB., WangY.X., and YouJ., J. Chem. Res., 2007, 662.
9.
WangY.X., ZhuY.K., LiuB., and YouJ., J. Chem. Res., 2008, 83.
10.
KanemasaS., OderaotoshiY., TanakaJ., J. Am. Chem. Soc., 1998, 120, 12355.
11.
GothelfK.V., and JørgensenK.A., Synthetic applications of 1,3-dipolar cycloaddition chemistry toward heterocycles and natural products, John Wiley & Sons, Inc.2002, p. 818.
12.
InoueM., SuzukiT., KinoshitaA., and NakadaM., Chem. Rec., 2008, 108, 169.
13.
GothelfK.V., HazellR.G., and JorgensenK.A., J. Org. Chem., 1996, 61, 346.
14.
GothelfK.V., HazellR.G., and JorgensenK.A., J. Org. Chem., 1998, 63, 5483.
15.
PosnerG.H., and DaiH.Y., Bull. J. Org. Chem., 1996, 61, 671.
16.
GentemannS., AlbanezeJ., and RamonG.F., J. Am. Chem. Soc., 1994, 116, 281.
17.
AdhikariR.M., MondalR., and ShahB. K, J. Org. Chem., 2007, 72, 4727.
18.
BritovsekG.P., GibsonV.C., and HoarauO.D., Inorg. Chem., 2003, 42, 3454.
19.
InoueM., and NakadaM., Org. Lett., 2004, 6, 2977.
20.
SuzukiT., KinoshitaA., and KawadaH., Synlett., 2003, 570.
21.
JorgensenK.A., and GothelfK.V., Helv. Chim. Acta, 1997, 80, 2039.
22.
GothelfK.V., and JorgensenK.A., J. Org. Chem., 1995, 60, 6847.
