145285-56-9Relevant academic research and scientific papers
Asymmetric dihydroxylation route to a dipeptide isostere of a protease inhibitor: Enantioselective synthesis of the core unit of ritonavir
Ghosh, Arun K.,Shin, Dongwoo,Mathivanan, Packiarajan
, p. 1025 - 1026 (1999)
An enantioselective synthesis of the dipeptide isostere of ritonavir has been accomplished utilizing Sharpless asymmetric hydroxylation as the key step.
Highly Regioselective Difluoroalkylarylation of Butadiene through a Nickel-Catalyzed Tandem Radical Process
Ma, Shucheng,Li, Fangjie,Zhang, Guisheng,Shi, Lei,Wang, Xiaoming
, p. 14848 - 14853 (2021/12/09)
A nickel-catalyzed reaction of 1,3-butadiene with easily accessible difluoroalkyl bromides and arylboronic acids has been realized, affording the corresponding 1,4-difluoroalkylarylation products in good yields with high regioselectivities. The procedure can also be successfully extended to nonfluorinated alkyl bromides. A radical clock experiment suggests that a key alkyl radical is involved in the catalysis. The operational simplicity, excellent functional-group compatibility, and high efficiency should make this nickel-catalyzed three-component reaction highly promising for the cost-efficient synthesis of difluoroalkylated compounds.
NiH-Catalyzed Proximal-Selective Hydroamination of Unactivated Alkenes
Jeon, Jinwon,Lee, Changseok,Seo, Huiyeong,Hong, Sungwoo
, p. 20470 - 20480 (2020/11/27)
Reported herein is a modular, NiH-catalyzed system capable of proximal-selective hydroamination of unactivated alkenes with diverse amine sources. The key to the successful implementation of this approach is the promotion of NiH insertion into even highly substituted olefins via coordination of the bidentate directing group to the nickel complex. A wide range of primary and secondary amines can be installed in both internal and terminal unactivated alkenes with excellent regiocontrol under the optimized reaction conditions. This protocol is flexible and general for the preparation of a variety of valuable β- and γ-amino acid building blocks that would otherwise be difficult to synthesize. The utility of this transformation was further demonstrated by the site-selective late-stage modification of complex and medicinally relevant molecules. Combined experimental and computational studies illuminate the detailed reaction mechanism.
Lewis Base/Br?nsted Acid Co-Catalyzed Asymmetric Thiolation of Alkenes with Acid-Controlled Divergent Regioselectivity
Luo, Hui-Yun,Dong, Jia-Wei,Xie, Yu-Yang,Song, Xu-Feng,Zhu, Deng,Ding, Tongmei,Liu, Yuanyuan,Chen, Zhi-Min
, p. 15411 - 15418 (2019/11/14)
A divergent strategy for the facile preparation of various enantioenriched phenylthio-substituted lactones was developed based on Lewis base/Br?nsted acid co-catalyzed thiolation of homoallylic acids. The acid-controlled regiodivergent cyclization (6-endo vs. 5-exo) and acid-mediated stereoselective rearrangement of phenylthio-substituted lactones were explored. Experimental and computational studies were performed to clarify the origins of the regioselectivity and enantioselectivity. The calculation results suggest that C?O and C?S bond formation might occur simultaneously, without formation of a commonly supposed catalyst-coordinated thiiranium ion intermediate and the potential π–π stacking between substrate and SPh as an important factor in the enantio-determining step. Finally, this methodology was applied in the rapid syntheses of the bioactive natural products (+)-ricciocarpin A and (R)-dodecan-4-olide.
Ring-Opening of Vinylcyclopropane-1,1-dicarboxylates by Boronic Acids under Ligandless Palladium Catalysis in Neat Water
Yin, JieXiang,Hyland, Christopher J. T.
, p. 6529 - 6536 (2015/10/06)
We report a highly efficient ring-opening reaction of vinylcyclopropanes by boronic acids in water, using palladium nanoparticles formed from Pd(OAc)2 under ligandless conditions. Unsubstituted vinylcyclopropanes provide linear addition products with high selectivity, while a switch in regioselectivity to branched products is observed for aryl-substituted vinylcyclopropanes.
