The osmium-catalyzed aminohydroxylation of Baylis-Hillman olefins

Tetrahedron Letters

Volumn 40, Issue 28, 1999, Pages 5151-5154

  Pringle, Wallace ^a   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Amino alcohols; Bayils Hillman reactions; Catalysis; Osmylations

Indexed keywords

ALKENE DERIVATIVE; AMINOALCOHOL; OSMIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DIASTEREOISOMER; HYDROXYLATION; POLYMERIZATION; SYNTHESIS; THIN LAYER CHROMATOGRAPHY; X RAY CRYSTALLOGRAPHY;

EID: 0033538666     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00887-4     Document Type: Article

References (14)

1. (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451.
2. (b) Kolb, H. C.; Sharpless, K. B. Asymmetric aminohydroxylation; in Transition Metals for Fine Chemicals and Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley-VCH: New York; in press.
3. (c) Schlingloff, G.; Sharpless, K. B. Asymmetric aminohydroxylation; in Asymmetric Oxidation Reactions: A Practical Approach; Katsuki, T., Ed.; Oxford University Press: Oxford; in press.
4. Rubin A. E.; Sharpless K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 2637.
5. For reviews on the Baylis-Hillman reaction see: (a) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
6. (b) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653 .
7. For recent advances of the Baylis-Hillman reaction see: (a) Kawamura, M; Kobayashi, S. Tetrahedron Lett. 1999, 40, 1539.
8. (b) Kataoka, T.; Iwama, T.; Kinoshita, H.; Tsujiyama, S.; Tsurukami, Y.; Iwamure, T.; Watanabe, S. Synlett 1999, 197.
9. (c) Kataoka, T.; Iwama, T.; Tsujiyama, S. Chem. Commun. 1998, 197.
10. (d) Aggarwal, V. K.; Tarver, G. J.; McCague, R. Chem. Commun. 1996, 2713.
11. 2O (1:1 v/v) is also a suitable solvent system for this reaction.
12. This syn selectivity is consistent with that observed in the osmium-catalyzed dihydroxylation of this class of olefins see: Bernardi, A.; Cardani, S.; Scolastico, C.; Villa, R. Tetrahedron 1988, 44, 491.
13. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017.
14. Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2810.