54443-82-2Relevant academic research and scientific papers
Method for synthesizing photoactive bromohydrin compound
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Paragraph 0182-0183; 0186-0187, (2021/07/21)
The invention discloses a method for synthesizing a photoactive bromohydrin compound, which comprises the following steps: reacting cinnamyl alcohol as shown in a formula I, benzamide bromide as shown in a formula II, a quinine derivative, L-camphorsulfonic acid and water in a first organic solvent to obtain the bromohydrin compound as shown in a formula III. According to the method, raw materials are easy to synthesize, reaction conditions are mild, operation is easy and convenient, the yield reaches up to 47%-87%, enantioselectivity can generally reach 80% or above, and the highest point can even reach 95%.
Stereoselective and Site-Specific Allylic Alkylation of Amino Acids and Small Peptides via a Pd/Cu Dual Catalysis
Huo, Xiaohong,He, Rui,Fu, Jingke,Zhang, Jiacheng,Yang, Guoqiang,Zhang, Wanbin
supporting information, p. 9819 - 9822 (2017/08/02)
We report a stereoselective and site-specific allylic alkylation of Schiff base activated amino acids and small peptides via a Pd/Cu dual catalysis. A range of noncoded α,α-dialkyl α-amino acids were easily synthesized in high yields and with excellent enantioselectivities (up to >99% ee). Furthermore, a direct and highly stereoselective synthesis of small peptides with enantiopure α-alkyl or α,α-dialkyl α-amino acids residues incorporated at specific sites was accomplished using this dual catalyst system.
A Simple and Efficient Access to Naphtho[b]furans by Claisen Rearrangement/Cyclization of Bromonaphthyl 3-Phenylallyl Ethers
Wang, Wei,Huang, Jin,Zhou, Rong,Jiang, Zhi-Jie,Fu, Hai-Yan,Zheng, Xue-Li,Chen, Hua,Li, Rui-Xiang
supporting information, p. 2442 - 2446 (2015/08/18)
A transition-metal-free Claisen rearrangement/cyclization reaction was developed for the synthesis of naphthofuran derivatives from bromonaphthyl 3-phenylallyl ethers. The nature of the base employed in this reaction plays an important role in determining the ratio for the formation of naphthofuran and naphthol products. By using K2CO3 as base and DMF as solvent, we have synthesized a variety of functionalized naphthofurans in good to high yields (49-92 %) and with satisfactory selectivities.
Preparation of Boc-protected cinnamyl-type alcohols: A comparison of the Suzuki-Miyaura coupling, cross-metathesis, and Horner-Wadsworth-Emmons approaches and their merit in parallel synthesis
Stambasky, Jan,Malkov, Andrei V.,Kocovsky, Pavel
experimental part, p. 705 - 732 (2009/04/03)
Three synthetic strategies for the construction of tert-butyl (E)-3-arylprop-2-en-1-ol carbonates are described. Complementary approaches employing Suzuki-Miyaura coupling and cross-metathesis reaction gave moderate yields of the title compounds in one-step, both methods are suitable for high-throughput and parallel chemistry. A detailed investigation into the Suzuki-Miyaura coupling reaction is provided along with the studies on the synthesis of pinacolyl 1-(tert-butyloxycarbonyl)propenol-3-ylboronate, the key building block. Conventional synthesis of the title compounds via the Horner-Wadsworth-Emmons reaction as a key step in a three-step-one-purification protocol was optimized and the results are compared with those of the latter reactions.
