User:Hkang10/sandbox2
history
[edit]Hydrogenation has a relatively long history in organic synthesis. At the end of the 19th century, P. Sabitier initiated the hydrogenation using fine metal particles in the heterogeneous catalytic system [1]. In 1961, the hydrogenation of olefins were also achieved in the homogenous catalytic system using RuCl3 by B.R. James and co-workers [2]However, any of the reactions could achieve a significant stereoselectivity until 1971 when H. B. Kagan introduced DIOP, a chiral diphosphane ligand. The DIOP-Rh complex was used for the asymmetric hydrogenation of dehydro amino acid and could achieve 72% ee[3].
In 1980, Noyori introduced a cationic BINAP-Rh catalyst for the asymmetric hydrogenation of olefin. The Rh catalyst could achieve high ee(>90%), but the reaction was relatively slow and only worked under specific conditions. The scope of the reaction was also limited to the stereoselective hydrogenation of α-(acylamino)-acrylic acid or esters to make amino acid derivatives.[4] In 1986, Noyori and coworkers discovered the BINAP-Ru dicarboxylate catalyst. The scope of the asymmetric hydrogenation was not limited to the synthesis of amino acid derivatives anymore, but also the hydrogenation of α,β- and β,γ- unsaturated carboxylic acids[5] and allyric/homoallyric alcohols with high ee around 90%.[6]
In 1991, Noyori and coworkers also found that the BINAP-Ru dihalide can catalyze the asymmetric hydrogenation of various functionalized ketones.[7]. While the BINAP-Ru dicarboxylate could only efficiently catalyze the hydrogenation of olefins, the BINAP-Ru dihalide could effectively catalyze both the hydrogenation of olefins and functionalized C=O bond[8].
Even though the BINAP-Ru dihalide catalyst functionalized ketone, the hydrogenation of simple ketone was remaind as problem to solve. Since 1953, H. C Brown and coworkers have succesfully achieved and developed the chemo-, and stereo-selective reduction of C=O bond. The chemoselectivity over C=C bond was achieved using NaBH4[9], the diastereoselectivity was achieved using Selectrides[10], and enantioselectivity was achieved using chiral stoichiometric reagents.[11]. However, all three selectivities could not be achieved at the same time. In 1995, Noyori has discovered that the RuCl2(phosphane)2(diamine)2 complex can catalyze the hydrogenation of unfunctionalized ketones[12]. This system also had chemoselectivity on C=O bond over the more reactive C=C bond.[13] The diastereoselectivity[14] and the enantioselectivity[15] could be achieved as well.
- ^ Noyori, R. (2002), "Asymmetric Catalysis: Science and Opportunities (Nobel Lecture)", Angewandte Chemie International Edition, 41 (12): 2008–22, doi:10.1002/1521-3773(20020617)41:12<2008::aid-anie2008>3.0.co;2-4, PMID 19746595
- ^ Halpern, J.; Harrod, J. F.; James, B. R. (1961), "Homogeneous Catalytic Hydrogenation of Olefinic Compounds", Journal of the American Chemical Society, 83 (3): 753–754, doi:10.1021/ja01464a055
{{citation}}: CS1 maint: multiple names: authors list (link) - ^ Dang, T. P.; Kagan, H. B. (1971), "The asymmetric synthesis of hydratropic acid and amino-acids by homogeneous catalytic hydrogenation", Journal of the Chemical Society D: Chemical Communications (10): 481, doi:10.1039/C29710000481
{{citation}}: CS1 maint: multiple names: authors list (link) - ^ Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. (1980), "Synthesis of 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP), an atropisomeric chiral bis(triaryl)phosphine, and its use in the rhodium(I)-catalyzed asymmetric hydrogenation of .alpha.-(acylamino)acrylic acids", Journal of the American Chemical Society, 102 (27): 7932–7934, doi:10.1021/ja00547a020
{{citation}}: CS1 maint: multiple names: authors list (link) - ^ Ohta, T.; Takaya, H.; Kitamura, M.; Nagai, K.; Noyori, R. (1987), "Asymmetric hydrogenation of unsaturated carboxylic acids catalyzed by BINAP-ruthenium(II) complexes", The Journal of Organic Chemistry, 52 (14): 3174–3176, doi:10.1021/jo00390a043
{{citation}}: CS1 maint: multiple names: authors list (link) - ^ Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori, R. (1987), "Enantioselective hydrogenation of allylic and homoallylic alcohols", Journal of the American Chemical Society, 109 (5): 1596–1597, doi:10.1021/ja00239a065
{{citation}}: CS1 maint: multiple names: authors list (link) - ^ Mashima, K.; Kusano, K.-h.; Sato, N.; Matsumura, Y.-i.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T. (1994), "Cationic BINAP-Ru(II) Halide Complexes: Highly Efficient Catalysts for Stereoselective Asymmetric Hydrogenation of .alpha.- and .beta.-Functionalized Ketones", The Journal of Organic Chemistry, 59 (11): 3064–3076, doi:10.1021/jo00090a026
{{citation}}: CS1 maint: multiple names: authors list (link) - ^ Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. (1988), "Homogeneous asymmetric hydrogenation of functionalized ketones", Journal of the American Chemical Society, 110 (2): 629–631, doi:10.1021/ja00210a070
{{citation}}: CS1 maint: multiple names: authors list (link) - ^ Schlesinger, H. I.; Brown, H. C.; Hoekstra, H. R.; Rapp, L. R. (1953), "Reactions of Diborane with Alkali Metal Hydrides and Their Addition Compounds. New Syntheses of Borohydrides. Sodium and Potassium Borohydrides1", Journal of the American Chemical Society, 75: 199–204, doi:10.1021/ja01097a053
{{citation}}: CS1 maint: multiple names: authors list (link) - ^ Brown, H. C.; Krishnamurthy, S. (1972), "Lithium tri-sec-butylborohydride. New reagent for the reduction of cyclic and bicyclic ketones with super stereoselectivity. Remarkably simple and practical procedure for the conversion of ketones to alcohols in exceptionally high stereochemical purity", Journal of the American Chemical Society, 94 (20): 7159–7161, doi:10.1021/ja00775a053
{{citation}}: CS1 maint: multiple names: authors list (link) - ^ Ramachandran, P. V.;,Brown, H. C.journal=ACS Symposium Series (1996), "Recent Advances in Asymmetric Reductions withB-Chlorodiisopinocampheylborane", Recent Advances in Asymmetric Reductions with B-Chlorodiisopinocampheylborane, ACS Symposium Series, vol. 641, pp. 84–97, doi:10.1021/bk-1996-0641.ch005, ISBN 0-8412-3381-0
{{citation}}: CS1 maint: multiple names: authors list (link) - ^ Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. (1995), "Practical Enantioselective Hydrogenation of Aromatic Ketones", Journal of the American Chemical Society, 117 (9): 2675–2676, doi:10.1021/ja00114a043
{{citation}}: CS1 maint: multiple names: authors list (link) - ^ Cite error: The named reference
citation 31was invoked but never defined (see the help page). - ^ Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. (1996), "Stereoselective Hydrogenation of Simple Ketones Catalyzed by Ruthenium(II) Complexes", The Journal of Organic Chemistry, 61 (15): 4872–4873, doi:10.1021/jo960997h
{{citation}}: CS1 maint: multiple names: authors list (link) - ^ Cite error: The named reference
citation 3was invoked but never defined (see the help page).