A dramatic reversal of facial selectivity in the Sharpless asymmetric dihydroxylation of a sterically hindered 3-methylidene-benzofuran

Tetrahedron Letters

Volumn 37, Issue 9, 1996, Pages 1375-1376

  Krysan, Damian J ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0029985249     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00057-3     Document Type: Article

References (10)

1. Kolb, H.C.; VanNieuwenhze, M.S.; Sharpless, K.B. Chem. Rev. 1994, 94, 2483.
2. Ayers, T.A.; Marciniak, G.; Schnettler, R.N. manuscript in preparation.
3. 1 The use of the less costly p-toluenesulfonamide in place of the usual methanesulfonamide did not affect the ee.
4. Crispino, G.A.; Jeong, K.-S.; Kolb, H.C.; Wang, Z.-M; Xu, D.; Sharpless, K.B. J. Org. Chem. 1993, 58, 3785.
5. Sharpless, K.B.; Amberg, W.; Bennani, Y.L.; Crispino, G.A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
6. (a) Vanhessche, K.P.M. and Sharpless, K.B., personal communication,
7. 5 while the PYR ligand selecitivity was counter to that predicted by the mnemonic.
8. (a) Kolb, H.C.; Andersson, P.G.; Sharpless, K.B. J. Am. Chem. Soc. 1994, 116, 1278.
9. (b) Norrby, P.-O.; Kolb, H.C.; Sharpless, K.B. J. Am. Chem. Soc. 1994, 116, 8470.
10. (c) Corey, E.J.; Noe, M.C.; Grogan, M. J. Tetrahedron Lett. 1994, 35, 6427 and references therein.