60733-10-0Relevant academic research and scientific papers
Regio- And Stereoselective Addition of HO/OOH to Allylic Alcohols
Wang, Xiao-Tao,Han, Wei-Bo,Chen, Hui-Jun,Zha, Qinghong,Wu, Yikang
, p. 10007 - 10021 (2020/08/28)
A range of allylic alcohols are shown to readily react with ethereal H2O2 in the presence of catalytic amounts of Na2MoO4-gly or MoO2(acac)2, affording the C═C trans hydroxylation-hydroperoxylation products in good yields with high regio- and stereoselect
Enantioselective Hydrogenation of Ketones using Different Metal Complexes with a Chiral PNP Pincer Ligand
Garbe, Marcel,Wei, Zhihong,Tannert, Bianca,Spannenberg, Anke,Jiao, Haijun,Bachmann, Stephan,Scalone, Michelangelo,Junge, Kathrin,Beller, Matthias
supporting information, p. 1913 - 1920 (2019/03/13)
The synthesis of different metal pincer complexes coordinating to the chiral PNP ligand bis(2-((2R,5R)-2,5-dimethyl-phospholanoethyl))amine is described in detail. The characterized complexes with Mn, Fe, Re and Ru as metal centers showed good activities regarding the reduction of several prochiral ketones. Comparing these catalysts, the non-noble metal complexes produced best selectivities not only for aromatic substrates, but also for different kinds of aliphatic ones leading to enantioselectivities up to 99% ee. Theoretical investigations elucidated the mechanism and rationalized the selectivity. (Figure presented.).
CHIRAL METAL COMPLEX COMPOUNDS
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Page/Page column 18; 19; 21; 23; 24; 29, (2018/11/10)
The invention comprises novel chiral metal complex compounds of the formula (I) wherein M, PR2, R3 and R4 are outlined in the description, its stereoisomers, in the form as a neutral complex or a complex cation with a suitable counter ion. The chiral metal complex compounds can be used in asymmetric reactions, particularly in asymmetric reductions of ketones, imines or oximes.
Manganese(I)-Catalyzed Enantioselective Hydrogenation of Ketones Using a Defined Chiral PNP Pincer Ligand
Garbe, Marcel,Junge, Kathrin,Walker, Svenja,Wei, Zhihong,Jiao, Haijun,Spannenberg, Anke,Bachmann, Stephan,Scalone, Michelangelo,Beller, Matthias
supporting information, p. 11237 - 11241 (2017/09/02)
A new chiral manganese PNP pincer complex is described. The asymmetric hydrogenation of several prochiral ketones with molecular hydrogen in the presence of this complex proceeds under mild conditions (30–40 °C, 4 h, 30 bar H2). Besides high catalytic activity for aromatic substrates, aliphatic ketones are hydrogenated with remarkable selectivity (e.r. up to 92:8). DFT calculations support an outer sphere hydrogenation mechanism as well as the experimentally determined stereochemistry.
Synthesis of chiral building blocks for oxygenated terpenoids through a simultaneous and stereocontrolled construction of contiguous quaternary stereocenters by an ireland-claisen rearrangement
Akahori, Yoshihiro,Yamakoshi, Hiroyuki,Sawayama, Yuki,Hashimoto, Shunichi,Nakamura, Seiichi
, p. 720 - 735 (2014/04/03)
Methods for highly stereocontrolled syntheses of chiral building blocks with a triad of contiguous stereocenters, including two quaternary ones, have been developed. Ireland-Claisen rearrangement of the (Z)-silyl ketene acetal generated stereoselectively
Enzyme- and ruthenium-catalyzed dynamic kinetic resolution of functionalized cyclic allylic alcohols
Lihammar, Richard,Millet, Renaud,Baeckvall, Jan-E.
, p. 12114 - 12120 (2014/01/06)
Enantioselective synthesis of functionalized cyclic allylic alcohols via dynamic kinetic resolution has been developed. Cyclopentadienylruthenium catalysts were used for the racemization, and lipase PS-IM or CALB was employed for the resolution. By optimization of the reaction conditions the formation of the enone byproduct was minimized, making it possible to prepare a range of optically active functionalized allylic alcohols in good yields and high ee's.
Stereo- and regioselectivity in the P450-catalyzed oxidative tandem difunctionalization of 1-methylcyclohexene
Roiban, Gheorghe-Doru,Agudo, Rubén,Reetz, Manfred T.
, p. 5306 - 5311 (2013/07/05)
The selective partial oxidation of small non-functionalized molecules using biocatalysis based on P450 monooxygenases is known to be difficult due to the expected poor regio- and stereoselectivity, but in this study it was nevertheless attempted. 1-Methyl
Mild two-step process for the transition-metal-free synthesis of carbon-carbon bonds from allylic alcohols/ethers and grignard reagents
Han, Xinping,Zhang, Yanhua,Wu, Jimmy
body text, p. 4104 - 4106 (2010/05/15)
Chemical Equation Represented A mild two-step process for the regioselective, transition-metal-free preparation of carbon-carbon bonds from allylic alcohols/ethers and Grignard reagents is described. This process obviates the need for the harsh deprotecti
ASYMMETRIC CATALYTIC HYDROGENATION OF PROCHIRAL KETONES AND ALDEHYDES
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Page/Page column 27, (2010/11/28)
Process for stereoselective hydrogenation by reacting racemic aldehydes or ketones having a stereogenic carbon atom in the position relative to the C(O) group and containing the structural element -(O)C-C-CH- by means of hydrogen in the presence of a base and a ruthenium complex containing a bidentate ligand having coordinating P and N atoms, a monophosphine ligand and anionic and/or uncharged ligands as homogeneous catalyst, with the charge being balanced by one or two monovalent acid anions or a divalent acid anion when uncharged ligands are present.
Enantioselective microbial oxidation of allyl alcohols
Matsumoto, Kazutsugu,Kawabata, Yoichi,Okada, Satoshi,Takahashi, Jun,Hashimoto, Key,Nagai, Yuto,Tatsuta, Junichi,Hatanaka, Minoru
, p. 1428 - 1429 (2008/03/18)
A new route to the optically active allyl alcohols by microbial oxidation is disclosed. Yamadazyma farinosa IFO 10896, a yeast, efficiently catalyzes the enantioselective oxidation of allyl alcohols to afford the corresponding optically active alcohols as the remaining substrates. This reaction is applicable to both cyclic and acyclic compounds. Copyright
