Abstract
Catalytic enantioselective oxygen transfer reactions have been a long-standing goal of synthetic chemistry. The use of molecular oxygen in these oxidations has engaged significant research efforts for decades. The present review considers the state of the art of aerobic asymmetric oxidations mediated by chiral organocatalysts and transition metal catalysts, occurring with formation of new
$\mathrm{C}$ -- $\mathrm{O}$ bonds, \textit{i.e}. oxygenations. The milestones and limitations of existing approaches are discussed, with focus on catalyst design and catalytic performance.
The bibliography includes 41 references.
Funders
Russian Foundation for Basic Research
16-29-10666
References
1.
rcr_87_9_821_bib1
Sigman
Curr. Opin. Drug Discov. Dev. ,
2002
2.
rcr_87_9_821_bib2
Ojima
2010
3.
rcr_87_9_821_bib3
Pellisier
2010
4.
Punniyamurthy T., Velusamy S., Iqbal J.
Chemical Reviews ,
2005
5.
Piera J., Bäckvall J.
Angewandte Chemie - International Edition ,
2008
6.
Roduner E., Kaim W., Sarkar B., Urlacher V.B., Pleiss J., Gläser R., Einicke W., Sprenger G.A., Beifuß U., Klemm E., Liebner C., Hieronymus H., Hsu S., Plietker B., Laschat S., et. al.
ChemCatChem ,
2012
7.
Masui M., Ando A., Shioiri T.
Tetrahedron Letters ,
1988
8.
Sim S.D., Wang M., Zhao Y.
ACS Catalysis ,
2015
9.
de Vries E.F., Ploeg L., Colao M., Brussee J., van der Gen A.
Tetrahedron Asymmetry ,
1995
10.
Lian M., Li Z., Cai Y., Meng Q., Gao Z.
Chemistry - An Asian Journal ,
2012
11.
Wang Y., Zheng Z., Lian M., Yin H., Zhao J., Meng Q., Gao Z.
Green Chemistry ,
2016
12.
Wang Y., Yin H., Tang X., Wu Y., Meng Q., Gao Z.
Journal of Organic Chemistry ,
2016
13.
Catalytic asymmetric hydroxylation of oxindoles by molecular oxygen using a phase-transfer catalyst.
Sano D., Nagata K., Itoh T.
Organic Letters ,
2008
14.
Yang Y., Moinodeen F., Chin W., Ma T., Jiang Z., Tan C.
Organic Letters ,
2012
15.
Córdova A., Sundén H., Engqvist M., Ibrahem I., Casas J.
Journal of the American Chemical Society ,
2004
16.
Sundén H., Engqvist M., Casas J., Ibrahem I., Córdova A.
Angewandte Chemie - International Edition ,
2004
17.
Ibrahem I., Zhao G., Sundén H., Córdova A.
Tetrahedron Letters ,
2006
18.
Kawai H., Okusu S., Yuan Z., Tokunaga E., Yamano A., Shiro M., Shibata N.
Angewandte Chemie - International Edition ,
2013
19.
Yamada T., Imagawa K., Nagata T., Mukaiyama T.
Chemistry Letters ,
1992
20.
rcr_87_9_821_bib20
Lee
Bull. K orean Chem. Soc. ,
1997
21.
Mukaiyama T., Yamada T., Nagata T., Imagawa K.
Chemistry Letters ,
1993
22.
Nagata T., Imagawa K., Yamada T., Mukaiyama T.
Chemistry Letters ,
1994
23.
rcr_87_9_821_bib23
Pozzi
1998
24.
Yamada T., Imagawa K., Nagata T., Mukaiyama T.
Bulletin of the Chemical Society of Japan ,
1994
25.
Rhodes B., Rowling S., Tidswell P., Woodward S., Brown S.M.
Journal of Molecular Catalysis A Chemical ,
1997
26.
Nagata T., Imagawa K., Yamada T., Mukaiyama T.
Bulletin of the Chemical Society of Japan ,
1995
27.
Nagata T., Imagawa K., Yamada T., Mukaiyama T.
Inorganica Chimica Acta ,
1994
28.
Kureshy R.I., Khan N.H., Abdi S.H., Iyer P., Bhatt A.K.
Journal of Molecular Catalysis A Chemical ,
1998
29.
Hadian-Dehkordi L., Hosseini-Monfared H.
Green Chemistry ,
2016
30.
Kureshy R.I., Khan N.H., Abdi S.H., Iyer P.
Journal of Molecular Catalysis A Chemical ,
1997
31.
rcr_87_9_821_bib31
Lai
1998
32.
Tanaka H., Nishikawa H., Uchida T., Katsuki T.
Journal of the American Chemical Society ,
2010
33.
Koya S., Nishioka Y., Mizoguchi H., Uchida T., Katsuki T.
Angewandte Chemie - International Edition ,
2012
34.
Bolm C., Schlingloff G., Weickhardt K.
1994
35.
Peng Y., Feng* X., Yu K., Li Z., Jiang* Y., Yeung C.
Journal of Organometallic Chemistry ,
2001
36.
rcr_87_9_821_bib36
Bolm
1995
37.
rcr_87_9_821_bib37
Bolm
1997
38.
Döbler C., Mehltretter G., Beller M.
Angewandte Chemie - International Edition ,
1999
39.
Döbler C., Mehltretter G.M., Sundermeier U., Beller M.
Journal of Organometallic Chemistry ,
2001
40.
Imagawa K., Nagata T., Yamada T., Mukaiyama T.
Chemistry Letters ,
1995
41.
Nagata T., Imagawa K., Yamada T., Mukaiyama T.
Bulletin of the Chemical Society of Japan ,
1995