- A Simple, Mild and General Oxidation of Alcohols to Aldehydes or Ketones by SO2F2/K2CO3 Using DMSO as Solvent and Oxidant
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A practical, general and mild oxidation of primary and secondary alcohols to carbonyl compounds proceeds in yields of up to 99% using SO2F2 as electrophile in DMSO as both the oxidant and the solvent at ambient temperature. No moisture- and oxygen-free conditions are required. Stoichiometric amount of inexpensive K2CO3, which generates easy to separate by-products, is used as the base. Thus, 5-gram scale runs proceeded in nearly quantitative yields by a simple filtration as the work-up. The use of a polar solvent such as DMSO, which usually promotes competing Pummerer rearrangement, is also noteworthy. This protocol is compatible with a variety of common N-, O-, and S-functional groups on (hetero)arene, alkene and alkyne substrates (68 examples). The protocol was applied (99% yield) to a formal synthesis of the important cholesterol-lowering drug Rosuvastatin. (Figure presented.).
- Zha, Gao-Feng,Fang, Wan-Yin,Leng, Jing,Qin, Hua-Li
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supporting information
p. 2262 - 2267
(2019/04/17)
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- A Transition-Metal-Free One-Pot Cascade Process for Transformation of Primary Alcohols (RCH2OH) to Nitriles (RCN) Mediated by SO2F2
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A new transition-metal-free one-pot cascade process for the direct conversion of alcohols to nitriles was developed without introducing an “additional carbon atom”. This protocol allows transformations of readily available, inexpensive, and abundant alcohols to highly valuable nitriles.
- Jiang, Ying,Sun, Bing,Fang, Wan-Yin,Qin, Hua-Li
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supporting information
p. 3190 - 3194
(2019/05/21)
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- NiH-Catalyzed Reductive Relay Hydroalkylation: A Strategy for the Remote C(sp3)?H Alkylation of Alkenes
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The terminal-selective, remote C(sp3)?H alkylation of alkenes was achieved by a relay process combining NiH-catalyzed hydrometalation, chain walking, and alkylation. This method enables the construction of unfunctionalized C(sp3)?C(sp3) bonds under mild conditions from two simple feedstock chemicals, namely olefins and alkyl halides. The practical value of this transformation is further demonstrated by the large-scale and regioconvergent alkylation of isomeric mixtures of olefins at low catalyst loadings.
- Zhou, Fang,Zhu, Jin,Zhang, Yao,Zhu, Shaolin
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supporting information
p. 4058 - 4062
(2018/03/21)
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- UNIQUE HALOGEN-INDUCED CYCLIZATIONS, REAGENTS THEREFOR, AND COMPOUNDS PRODUCED THEREBY
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This disclosure is related to halonium compounds useful for cyclization of polyenes, alkenoic acids, and alkenyl alkyl ethers, and halogenation of aromatic compounds. The synthesis of such halonium compounds, compounds made using such halonium compounds, and synthesis of natural compounds, including decalins, using the halonium compounds is also disclosed. A representative halonium compound of the disclosure is: Formula (I).
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Page/Page column 149-150
(2012/04/04)
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- Design, synthesis, and biological evaluation of N-Alkylated deoxynojirimycin (DNJ) derivatives for the treatment of dengue virus infection
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We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENV) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENV in BHK cells of 6.5 μM, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure-activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 μM) against DENV infection, while maintaining low cytotoxicity (CC50 > 500 μM, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 α 4%).
- Yu, Wenquan,Gill, Tina,Wang, Lijuan,Du, Yanming,Ye, Hong,Qu, Xiaowang,Guo, Ju-Tao,Cuconati, Andrea,Zhao, Kang,Block, Timothy M.,Xu, Xiaodong,Chang, Jinhong
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supporting information; experimental part
p. 6061 - 6075
(2012/08/14)
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- A general strategy for the stereocontrolled preparation of diverse 8- and 9-membered Laurencia -type bromoethers
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A unique procedure to effect a ring-expanding bromoetherification process is described, wherein tetrahydrofurans and tetrahydropyrans are smoothly transformed into 8- and 9-membered bromoethers in a regio- and stereocontrolled manner through the use of BDSB (bromodiethylsulfonium bromopentachloroantimonate). These products resemble the cores of the Laurencia C15 acetogenins. In light of the generality and effectiveness of the approach, this work provides a unique strategy for their laboratory preparation and may implicate a possible biosynthesis pathway.
- Snyder, Scott A.,Treitler, Daniel S.,Brucks, Alexandria P.,Sattler, Wesley
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p. 15898 - 15901
(2011/11/13)
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