Abstract
Asymmetric dihydroxylation of olefinic groups is an extremely important synthetic transformation which has been widely utilized to obtain optically pure pharmaceuticals and other fine chemical products. In recent years,catalyst systems for the asymmetric C=C dihydroxylations have attracted significant interest, the major research efforts being focused on designing environmentally benign catalyst systems. This mini-review summarizes recent progress in the field, surveying both novel, less toxic modifications of the classical osmium-based catalysts, and the highly efficient and enantioselective non-osmium catalyst systems.
The bibliography includes 50 references.
Funders
Russian Foundation for Basic Research
16-29-10666
Ministry of Education and Science of the Russian Federation
AAAA-A17-117041710080-4
References
1.
Jacobsen E.N., Marko I., Mungall W.S., Schroeder G., Sharpless K.B.
Journal of the American Chemical Society ,
1988
2.
Kolb H.C., VanNieuwenhze M.S., Sharpless K.B.
Chemical Reviews ,
1994
3.
Heravi M.M., Zadsirjan V., Esfandyari M., Lashaki T.B.
Tetrahedron Asymmetry ,
2017
4.
Bebbington M.W.
Chemical Society Reviews ,
2017
5.
Trindade A.F., Gois P.M., Afonso C.A.
Chemical Reviews ,
2009
6.
Barbaro P., Liguori F.
Chemical Reviews ,
2008
7.
Srour H., Le Maux P., Chevance S., Simonneaux G.
Coordination Chemistry Reviews ,
2013
8.
Coombs J.R., Morken J.P.
Angewandte Chemie - International Edition ,
2016
9.
Talsi E.P., Bryliakov K.P.
Coordination Chemistry Reviews ,
2012
10.
rcr_88_11_1094_bib10
Tse
2009
11.
Bataille C.J., Donohoe T.J.
Chemical Society Reviews ,
2011
12.
Bryliakov K.P.
Chemical Reviews ,
2017
13.
rcr_88_11_1094_bib13
Zaytsev
Synthesis ,
2006
14.
Branco L., Ferreira F.C., Santos J., Crespo J., Afonso C.A.
Advanced Synthesis and Catalysis ,
2008
15.
Ferreira F.C., Branco L.C., Verma K.K., Crespo J.G., Afonso C.A.
Tetrahedron Asymmetry ,
2007
16.
Qiu S., Sun J., Li Y., Gao L.
Materials Research Bulletin ,
2011
17.
Balagam B., Mitra R., Richardson D.E.
Tetrahedron Letters ,
2008
18.
Periasamy M., Satish Kumar S., Sampath Kumar N.
Tetrahedron Letters ,
2008
19.
Junttila M.H., Hormi O.E.
Journal of Organic Chemistry ,
2007
20.
Methanesulfonamide: a Cosolvent and a General Acid Catalyst in Sharpless Asymmetric Dihydroxylations
Junttila M.H., Hormi O.O.
Journal of Organic Chemistry ,
2009
21.
Burghart-Stoll H., Böhnke O., Brückner R.
Organic Letters ,
2011
22.
Fristrup P., Tanner D., Norrby P.
Chirality ,
2003
23.
Weber F., Brückner R.
European Journal of Organic Chemistry ,
2015
24.
Dehury S.K., Hariharakrishnan V.S.
Tetrahedron Letters ,
2007
25.
Akiyama R., Matsuki N., Nomura H., Yoshida H., Yoshida T., Kobayashi S.
RSC Advances ,
2012
26.
Konieczny S., Leurs M., Tiller J.C.
ChemBioChem ,
2014
27.
Zhu J., Sun X., Wang X., Wu L.
ChemCatChem ,
2017
28.
Shilpa N., Manna J., Rana R.K.
European Journal of Inorganic Chemistry ,
2015
29.
Zhao Y., Xing X., Zhang S., Wang D.Z.
Organic and Biomolecular Chemistry ,
2014
30.
Xing X., Zhao Y., Xu C., Zhao X., Wang D.Z.
Tetrahedron ,
2012
31.
Gourdet B., Lam H.W.
Angewandte Chemie - International Edition ,
2010
32.
OsO4⋅Streptavidin: A Tunable Hybrid Catalyst for the Enantioselective cis-Dihydroxylation of Olefins
Köhler V., Mao J., Heinisch T., Pordea A., Sardo A., Wilson Y.M., Knörr L., Creus M., Prost J., Schirmer T., Ward T.R.
Angewandte Chemie - International Edition ,
2011
33.
Talero A., Burtoloso A.
Synlett ,
2017
34.
Costas M., Tipton A.K., Chen K., Jo D., Que L.
Journal of the American Chemical Society ,
2001
35.
Suzuki K., Oldenburg P., Que L.
Angewandte Chemie - International Edition ,
2008
36.
Zang C., Liu Y., Xu Z., Tse C., Guan X., Wei J., Huang J., Che C.
Angewandte Chemie - International Edition ,
2016
37.
Lyakin O.Y., Bryliakov K.P., Talsi E.P.
Coordination Chemistry Reviews ,
2019
38.
de Boer J.W., Browne W.R., Harutyunyan S.R., Bini L., Tiemersma-Wegman T.D., Alsters P.L., Hage R., Feringa B.L.
Chemical Communications ,
2008
39.
Chow T.W., Liu Y., Che C.
Chemical Communications ,
2011
40.
rcr_88_11_1094_bib40
Wang
JACS ,
2015
41.
rcr_88_11_1094_bib41
Hao
JACS ,
2016
42.
rcr_88_11_1094_bib42
Kliman
JACS ,
2009
43.
Rh-Catalyzed Enantioselective Diboration of Simple Alkenes: Reaction Development and Substrate Scope
Trudeau S., Morgan J.B., Shrestha M., Morken J.P.
Journal of Organic Chemistry ,
2005
44.
Toribatake K., Nishiyama H.
Angewandte Chemie - International Edition ,
2013
45.
Fang L., Yan L., Haeffner F., Morken J.P.
Journal of the American Chemical Society ,
2016
46.
Gally C., Nestl B.M., Hauer B.
Angewandte Chemie - International Edition ,
2015
47.
Xu Y., Jia X., Panke S., Li Z.
Chemical Communications ,
2009
48.
Xu Y., Li A., Jia X., Li Z.
Green Chemistry ,
2011
49.
Wu S., Chen Y., Xu Y., Li A., Xu Q., Glieder A., Li Z.
ACS Catalysis ,
2014
50.
Albrecht Ł., Jiang H., Dickmeiss G., Gschwend B., Hansen S.G., Jørgensen K.A.
Journal of the American Chemical Society ,
2010