Reversal of regioselection in the rearrangement of cinnamate diol cyclic iminocarbonates

Tetrahedron Letters

Volumn 41, Issue 11, 2000, Pages 1789-1792

  Cho, Gae Y ^a   Park, Jung Nam ^a   Ko, Soo Y ^a  

^a Ewha Womans University   (South Korea)

Author keywords

Asymmetric dihydroxylation; Cyclic iminocarbonate rearrangement; Regioselection

Indexed keywords

CINNAMIC ACID DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; HYDROXYLATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0342906193     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00017-4     Document Type: Article

References (9)

1. Cho, G. Y.; Ko, S. Y. J. Org. Chem. 1999, 64, 8745.
2. (a) Jacobsen, E. N.; Marko, I.; Mungall, W. S.; Schroder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968.
3. (b) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
4. (a) Li, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451.
5. (b) O'Brien, P. Angew. Chem., Int. Ed. Engl. 1999, 38, 326, and references cited therein.
6. The regioisomeric ratios given throughout this paper are those of the α:β-nitrogen isomers.
7. Synthetic applications for the reversed regioselective cyclic iminocarbonate rearrangement chemistry will be reported elsewhere.
8. Cho, G. Y.; Ko, S. Y., unpublished results.
9. cf. Tao, B.; Schlingloff, G.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 2507.