124988-64-3Relevant articles and documents
Enantioselective reduction of α-keto esters to 1,2-diols using the NaBH4/Me3SiCl system catalyzed by polymer-supported chiral sulfonamide
Wang, Guang-Yin,Hu, Jian-Bing,Zhao, Gang
, p. 807 - 810 (2004)
In the presence of 25mol% of a polymer-supported chiral sulfonamide, a variety of α-keto esters can be reduced into the corresponding 1,2-diols in good yields and high enantioselectivities using the NaBH4/Me 3SiCl reducing system.
Concise, scalable and enantioselective total synthesis of prostaglandins
Zhang, Fuhao,Zeng, Jingwen,Gao, Mohan,Wang, Linzhou,Chen, Gen-Qiang,Lu, Yixin,Zhang, Xumu
, p. 692 - 697 (2021/06/01)
Prostaglandins are among the most important natural isolates owing to their broad range of bioactivities and unique structures. However, current methods for the synthesis of prostaglandins suffer from low yields and lengthy steps. Here, we report a practicability-oriented synthetic strategy for the enantioselective and divergent synthesis of prostaglandins. In this approach, the multiply substituted five-membered rings in prostaglandins were constructed via the key enyne cycloisomerization with excellent selectivity (>20:1 d.r., 98% e.e.). The crucial chiral centre on the scaffold of the prostaglandins was installed using the asymmetric hydrogenation method (up to 98% yield and 98% e.e.). From our versatile common intermediates, a series of prostaglandins and related drugs could be produced in two steps, and fluprostenol could be prepared on a 20-gram scale. [Figure not available: see fulltext.]
Iron-Catalyzed Diborylation of Unactivated Aliphatic gem-Dihalogenoalkenes: Synthesis of 1,2-Bis(boryl)alkanes
Feng, Zhang,Liu, Zhengli,Pu, Yu,Zhang, Xiaoming,Zhou, Shangsheng,Zhu, Jiang
, p. 5565 - 5570 (2021/07/31)
Herein, we report the first example of iron-catalyzed defluoroborylation of unactivated gem-difluoroalkenes, gem-dichloroalkenes, and gem-dibromoalkenes, providing the 1,2-bis(boryl)alkanes in moderate to good yield. This transformation has high regiosele
Site-Selective Mono-Oxidation of 1,2-Bis(boronates)
Yan, Lu,Morken, James P.
supporting information, p. 3760 - 3763 (2019/05/24)
Site-selective oxidation of vicinal bis(boronates) is accomplished through the use of trimethylamine N-oxide in 1-butanol solvent. The reaction occurs with good efficiency and selectivity across a range of substrates, providing 2-hydro-1-boronic esters which are shown to be versatile intermediates in the synthesis of chiral building blocks.