76888-40-9Relevant academic research and scientific papers
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
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
A [3,3]-sigmatropic process catalysed by acetate. The decarboxylative Claisen rearrangement
Bourgeois, Damien,Craig, Donald,Grellepois, Fabienne,Mountford, David M.,Stewart, Alan J. W.
, p. 483 - 495 (2007/10/03)
Allylic tosylacetates and tosylmalonates undergo acetate-catalysed decarboxylative Claisen rearrangement in the presence of N,O-bis(trimethylsilyl) acetamide. The homoallylic sulfones formed in these transformations correspond to the products of regiospecific allylation of sulfone-stabilised carbanions. A mechanistic rationale is proposed.
Asymmetric peroxidation of prochiral allylic and benzylic compounds with tert-butyl hydroperoxide and chiral bisoxazoline-copper complexes
Schulz, Manfred,Kluge, Ralph,Gadissa Gelalcha, Feyissa
, p. 4341 - 4360 (2007/10/03)
The first enantioselective peroxidation of prochiral allylic and benzylic C-H compounds by the use of chiral bisoxazoline-copper(I) complexes, generated in situ from the ligands 3 and 4a-d, and t-BuOOH as oxidant is reported. Cyclohexene 1, cyclopentene 5, α-angelica lactone 7, allylbenzene 9 and 2-phenylbutane 11 were converted into the optically active allylic and benzylic tert-butyl peroxides 2, 6, 8, 10a and 12 in good yields and ee values of 4-20%. Oxidations of 1-substituted 1-cyclohexenes 13a-c led to mixtures of regioisomeric peroxides 16a-c, 17a-c and 18a-c with different regio- and enantioselectivities, depending on the 1-substituent and the ligand used. The highest ee values (up to 84%) were observed for (S)-3-tert- butylperoxy-1-methyl-1-cyclohexene 17a.
Lithium Aluminium Hydride Partially Decomposed with (-)-N-Methylephedrine and 2-Alkylaminopyridine: An Improved Chiral Hydride Useful for the Practical Asymmetric Reduction of Achiral Cyclic Ketones
Kawasaki, Motoji,Suzuki, Yasutaka,Terashima, Shiro
, p. 52 - 60 (2007/10/02)
The title chiral hydride was found to reduce various achiral cyclic ketons, giving the corresponding optically active cyclic (R)-alcohols in high optical (73-98percent) yields.The development of the improved chiral hydride and some characteristics of the reagent are also described.Keywords - asymmetric reduction; lithium aluminium hydride; (-)-N-methylephedrine; 2-alkylaminopyridine; 2-cyclohexen-1-one; achiral cyclic ketone; optically active cyclic alcohol
