The presence of an allylic alcohol facilitates ring-closing metathesis of sulfur-containing substrates with Grubbs’ dihydroimidazole ruthenium complex.
GrubbsR.H., and ChangS., Tetrahedron, 1998, 54, 4413; (c) Also see Adv. Synth. Catal., 2002, 344, issue 6-7 for an overview of metathesis in organic synthesis.
4.
(a) SchwabP., GrubbsR. H., and ZillerJ. W., J. Am. Chem. Soc., 1996, 118, 100.
5.
SchwabP., FranceM. B., ZillerJ. W., and GrubbsR. H., Angew. Chem., Int. Ed. Engl., 1995, 34, 2039.
6.
(a) BazanG.C., OskamJ. H., ChoH. N., ParkL. Y., and SchrockR. R., J. Am. Chem. Soc., 1991, 113, 6899.
7.
BazanG.C., KhosraviE., SchrockR. R., FeastW. J., GibsonV. C., OreganM. B., ThomasJ. K., and DavisW. M., J. Am. Chem. Soc., 1990, 112, 8378.
8.
(a) SchollM., DingS., LeeC. W., and GrubbsR. H., Org. Lett., 1999, 1, 953.
9.
TrnkaT.M., and GrubbsR. H., Acc. Chem. Res., 2001, 34, 18.
10.
(a) ShonY.S., and LeeT. R., Tetrahedron Lett., 1997, 38, 1283.
11.
MooreJ.D., SprottK. T., and HansonP. R., Synlett2001, 605.
AnandR.V., BaktharamanS., and SinghV. K., J. Org. Chem., 2003, 68, 3356. Note that alkenes containing sulfur functionality of higher oxidation states do undergo RCM.
15.
(a) HoyeT.R., and ZhaoH., Org. Lett., 1999, 1, 1123.
16.
MaishalT.K., Sinha-MahapatraD. K., ParanjapeK., and SarkarA., Tetrahedron Lett., 2002, 43, 2263.
17.
(a) AgerD.J., Chem. Soc. Rev., 1982, 11, 493.
18.
KirpichenkoS.V., SuslovaE. N., AlbanovA. I., and ShainyanB. A., Tetrahedron Lett., 1999, 40, 185.
19.
BalduzziS., and BrookM. A., Tetrahedron, 2000, 56, 1617.
20.
SanjiT., IwataM., WatanabeM., HoshiT., and SakuraiH., Organometallics, 1998, 17, 5068.
21.
(a) PaquetteL.A., EfremovI., TeubrevinG., and TeubrevinH., J. Am. Chem. Soc., 2001, 123, 4492.
22.
AckermannL., El TomD., and FürstnerA., Tetrahedron, 2000, 56, 2195.
23.
GurjarM.K., and YakambramP., Tetrahedron Lett., 2001, 42, 3633.
24.
ChangS., and GrubbsR. H., Tetrahedron Lett., 1997, 38, 4757.
