Baeyer-Villiger Oxidation
Follow-up reaction of Brown Hydroboration
Ozonolysis
Recent Literature
A clean and safe method for the dihydroxylation of alkenes under organic-solvent- and metal-free conditions was developed. The resin-supported sulfonic acid is easily recycled.
Y. Usui, K. Sato, M. Tanaka, Angew. Chem. Int. Ed., 2003, 42, 5623-5625.
Convenient methods for the preparation of stable and non-volatile mono- and dichloroborane adducts of dioxane from dioxane-BCl3 and NaBH4鹿晗行程 in the prence of catalytic amounts of tri- or tetraglyme were developed. The dioxane-monochloroborane adduct hydroborates reprentative olefins cleanly and rapidly and lead to the corresponding alcohols in quantitative yields after oxidation.
J. V. B. Kanth, H. C. Brown, 牛仔裤的夏天J. Org. Chem, 2001, 66, 5359-5365.
漫画与生活
A rhodium-catalyzed enantiolective syn addition of bis(catecholato)diboron to simple alkenes in the prence of (S)-Quinap provides enantioenriched 1,2-diols after subquent oxidation. The substrate scope, the reaction mechanism, and competing pathways are discusd.
S. Trudeau, J. M. Morgan, M. Shrestha, J. P. Morken, J. Org. Chem., 2005, 70, 9538-9544.
Pt-catalyzed enantiolective addition of bis(pinacolato)diboron (B2(pin)2) to conjugated dienes enables an asymmetric 1,4-dihydroxylation of 1,3-dienes. Dienes which are unable to adopt the S-cis conformation are unreactive. For most substrates, 1,4-addition is the predominant pathway.
H. E. Burks, L. T. Kliman, J. P. Morken, J. Am. Chem. Soc., 2009, 131, 9134-9135.
Lithiated epoxides react stereospecifically with boronates to give syn-1,2-diols, a process that can be ud iteratively to create triols containing four stereogenic centers.
E. Vedrenne, O. A. Wallner, M. Vitale, F. Schmidt, V. K. Aggarwal, Org. Lett., 2009, 11, 165-168.
A direct, mild ketohydroxylation of various 1-aryl-1-alkenes with H2O2, catalyzed by the inexpensive 12-tungstophosphoric acid/cetylpyridinium chloride system, gave acyloins in good yields and high regiolectivies.
Y. Zhang, Z. Shen, J. Tang, Y. Zhang, L. Kong, Y. Zhang, Org. Biomol. Chem., 2006, 4, 1478-1482.
An efficient epoxidation of a broad range of olefins using hydrogen peroxide as the oxidant has been accomplished in the prence of acetic acid and a mangane catalyst that exhibits an uncommon chemolectivity.
I. Garcia-Bosch, X. Ribas, M. Costas, Adv. Synth. Catal., 2008, 351, 348-352.
酸辣鸡胗A chiral bisaryl-silyl-protected pyrrolidine acts as a very lective epoxidation organocatalyst using simple oxidation agents. The scope of the reaction is demonstrated by the formation of optically active α,β-epoxy aldehydes in high yields and enantiolectivities. The asymmetric epoxidation reactions proceed also under environmental friendly reaction conditions in, for example, water mixtures of alcohols.
M. Marigo, J. Franzen, T. B. Pouln, W. Zhuang, K. A. Jorgenn, J. Am. Chem. Soc., 2005, 127, 6284-6289.
狮子座男生的性格An effective epoxidation of lipophilic alkenes using hydrogen peroxide was accomplished with a mangane sulfate/bicarbonate catalytic system in an ionic liquid at room temperature.
K.-H. Tong, K.-Y. Wong, T. H. Chan, Org. Lett., 2003, 5, 3423-3425.
An epoxidation of alkenes using hydrogen peroxide as the terminal oxidant is promoted by catalytic amounts (1.0-0.1 mol %) of mangane(2仲裁和诉讼有什么区别+) salts, and must be performed using at least catalytic amounts of bicarbonate buffer. Various aryl-substituted, cyclic, and trialkyl-substituted alkenes were epoxidized under the conditions using 10 equiv of hydrogen peroxide, but monoalkyl-alkenes were not. Additives such as sodium acetate and salicylic acid enhanced the rate of the desired epoxidation reaction by 2-3 times. Possible mechanisms for the reaction are discusd.
B. S. Lane, M. Vogt, V. J. DeRosa, K. Burgess, J. Am. Chem. Soc., 2002, 124, 11946-11954.
Aryl benzyl lenoxides are efficient catalysts for the epoxidation of various olefinic substrates and the Baeyer-Villiger oxidation of aldehydes and ketones with hydrogen peroxide.
M. A. Goodman, M. R. Detty, Synlett, 2006, 1100-1104.
A highly enantiolective catalytic epoxidation of α,β-unsaturated diaryl enones was achieved with high chemical yield by using aqueous hydrogen peroxide in the prence of a guanidine-urea bifunctional organocatalyst. The catalyst performs cooperatively by interaction of the guanidine group with hydrogen peroxide and the urea group with the enone or vice versa.
S. Tanaka, K. Nagasawa Synlett, 2009, 667-670.
Chiral primary amine salts catalyze highly enantiolective epoxidations of cyclic enones with hydrogen peroxide.
X. Wang, C. M. Reisinger, B. List, J. Am. Chem. Soc.每天的英文, 2008, 130, 6070-6071.
