Electrocatalytic asymmetric dihydroxylation of olefinic compound

Details Electrocatalytic asymmetric dihydroxylation of olefinic compound Electrocatalytic asymmetric dihydroxylation of olefinic compound

1994-01-18

1995-05-30

Niebling, John

Chemistry: electrical and wave energy

Processes and products

204 59R, 204 96, C25B 302

Patent

active

054198178

ABSTRACT:
A process is disclosed in which optically active glycols are produced through an electrolytic asymmetric dihydroxylation (ADH) reaction involving olefins as substrates. The ADH reaction is mediated by a catalytically active amount of osmium tetroxide or osmium-containing precursor in a protic medium in the presence of chiral ligand. Any lower valent osmium species produced in the course of the ADH reaction is regenerated electrolytically either directly in the absence of a secondary oxidant or indirectly in the presence of a secondary oxidant that itself undergoes electrolytic regeneration.

REFERENCES:
patent: 3488394 (1970-01-01), Cummins
patent: 3650918 (1972-03-01), Johnson et al.
patent: 3846478 (1974-11-01), Cummins
patent: 3953305 (1976-04-01), Connolly
patent: 4217291 (1980-08-01), Wu et al.
patent: 4278517 (1981-07-01), Abatjoglou
patent: 5126494 (1992-06-01), Gilheany et al.
patent: 5302257 (1994-04-01), Gao et al.
Devine and Oh (1992) J. Am. Chem. Soc. 57:396-399.
Sharpless et al. (1991) J. Org. Chem. 56: 4585-4588 and references cited therein.
Denis et al. (1990) J. Am. Chem. Soc. 55: 1957-1959.
Kwong et al. (1990) Tetrahedron Lett. 31: 2999-3002.
Wai et al. (1989) J. Am. Chem. Soc. 111: 1123-1125.
Jacobsen et al. (1988) J. Am. Chem. Soc. 110: 1968-1970.
Mukaiyama and Murakami (1987) Synthesis. 1043-1054.
Torii, S. (1985) "Electro-Organic Syntheses," 192-194 and 244-245.
Tomioka et al. (1987) J. Am. Chem. Soc. 109: 6213-6215.
Hentges and Sharpless (1980) J. Am. Chem. Soc. 102: 4263-4265.
Shepelin (1975) Chem Abstracts 82: 36521c.
Shepelin (1973) Novosti Elektrokhim. org. Soedin., Tezisy Dokl. Vses. Soveshch. Elektrokhim Org. Soedin., 8th Meeting: Feoktistov, L. G. (Ed), 1920 with English translation.
Mayell (1968) IEC Products Res. 7: 129-136.
McCormick et al. Tetrahedron Letters, 22: 607-610 (1981).
Lohray et al. Tetrahedron Letters, 30. 2041 (1989).
Hashiyama et al. J. Org. Chem., 57: 5067-5068 (1992-published after filing date of parent application).

Affiliated with

Also associated with

Rating

Electrocatalytic asymmetric dihydroxylation of olefinic compound does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Electrocatalytic asymmetric dihydroxylation of olefinic compound, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Electrocatalytic asymmetric dihydroxylation of olefinic compound will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-359361