4333-51-1Relevant academic research and scientific papers
Stereoselective Synthesis of Trisubstituted Vinylboronates from Ketone Enolates Triggered by 1,3-Metalate Rearrangement of Lithium Enolates
Hu, Yue,Sun, Wei,Zhang, Tao,Xu, Nuo,Xu, Jianeng,Lan, Yu,Liu, Chao
supporting information, p. 15813 - 15818 (2019/10/28)
An unprecedented stereoselective synthesis of trisubstituted vinylboronates is reported to proceed by direct borylation of lithium ketone enolates under transition-metal-free conditions. The stereospecific C?O borylation of lithium enolates was triggered by a carbonyl-induced 1,3-metalate rearrangement via a C-bound boron enolate. DFT calculations and control experiments revealed that the stereoselectivity is controlled by sterics. A variety of stereospecific trisubstituted vinylboronates, together with several tetrasubstituted vinylboronates, were conveniently synthesized with the newly developed methodology. Based on the transformation of stereospecific vinylboronate, a single isomer of Dienestrol was efficiently obtained.
Aluminum Chloride Promoted Cross-Coupling of Trisubstituted Enol Phosphates with Organozinc Reagents En Route to the Stereoselective Synthesis of Tamoxifen and Its Analogues
Kotek, Vladislav,Polák, Peter,Dvo?áková, Hana,Tobrman, Tomá?
supporting information, p. 5037 - 5044 (2016/10/26)
A new method for the stereoselective cross-coupling reaction of arylzinc chlorides with trisubstituted enol phosphates is described. The developed method requires aluminum chloride as a promoter, and the reaction conditions tolerate various functional groups. The observed reactivity pattern of trisubstituted enol phosphates was used for the stereoselective preparation of tamoxifen and its analogues.
Metal-free oxidative cross-coupling of diazirines with arylboronic acids
Wu, Guojiao,Zhao, Xia,Ji, Wenzhi,Zhang, Yan,Wang, Jianbo
, p. 1961 - 1963 (2016/02/05)
We report herein a metal-free cross-coupling of diazirines with arylboronic acids under oxidative conditions. The reaction affords a series of substituted olefins. It is proposed that the interaction between the nitrogen on diazirine with arylboronic acid plays a key role in this transformation.
