News&Event
Congratulation to Hongjuan Shen, Jingjie Li and Junkai Fu for their works were published on OL and CEJ respectively!
Recently, Hongjuan Shen, Jingjie Li and Junkai Fu’s works were published on Org Lett and Chem. Eur. J respectively!
Miss Hongjuan Shen’s work represented two novel methods to synthesis of dihydroisobenzofuran and indanone derivatives from 2-triazole-benzaldehydes and 2-triazole-alkylaryl ketones via rhodium(II)-catalyzed tandem reactions.
For more details, please see the paper online: https://web.pkusz.edu.cn/yang/86/ or Org. Lett., Article ASAP
Miss Jingjie Li’s work was published as an letter titled “Palladium-Catalyzed Oxidative Rearrangement of Tertiary Allylic Alcohols to Enones with Oxygen in Aqueous Solvent”. In her work, a one-pot procedure for Pd(TFA)2-catalyzed 1,3-isomerization of tertiary allylic alcohols to secondary allylic alcohols followed by a Pd(TFA)2/neocuproine-catalyzed oxidative reaction to β-disubstituted-α,β-unsaturated kenones was developed.
For more details, please see the paper online: https://web.pkusz.edu.cn/yang/85/ or Org. Lett., 2014, 16, 5370
Mr. Junkai Fu’s work was focused on the 4-substituted-1-tosyl-1,2,3-triazole-based stereoselective synthesis of structurally diverse oxaspirocycles. The synthesis involves Rh-catalyzed loss of nitrogen from 4-substituted-1-tosyl-1,2,3-triazoles, Grignard reaction, and a ring-closing metathesis reaction as key steps.
For more details, please see the paper online: https://web.pkusz.edu.cn/yang/84/ or Chem. Eur. J. 2014, 20, 12881
86.Tunable and Chemoselective Syntheses of Dihydroisobenzofurans and Indanones via Rhodium-Catalyzed Tandem Reactions of 2‑Triazole-benzaldehydes and 2‑Triazole-alkylaryl Ketones
Hongjuan Shen, Junkai Fu, Jianxian Gong,* and Zhen Yang*
Two novel rhodium(II)-catalyzed tandem reactions were developed for the synthesis of dihydroisobenzofuran and indanone derivatives from 2-triazole-benzaldehydes and 2-triazole-alkylaryl ketones. Dihydroisobenzofuran derivatives were obtained in good yields with high regioselectivities when alcohols were used as nuclophiles in these reactions, whereas the replacement of the alcohol with water resulted in the diastereoselective formation of highly functionalized indanone derivatives.
85.Palladium-Catalyzed Oxidative Rearrangement of Tertiary Allylic Alcohols to Enones with Oxygen in Aqueous Solvent
Jingjie Li , Ceheng Tan , Jianxian Gong *, and Zhen Yang *
A one-pot procedure for Pd(TFA)2-catalyzed 1,3-isomerization of tertiary allylic alcohols to secondary allylic alcohols followed by a Pd(TFA)2/neocuproine-catalyzed oxidative reaction to β-disubstituted-α,β-unsaturated kenones was developed.
84.Concise Stereoselective Synthesis of Oxaspirocycles with 1-Tosyl-1,2,3-triazoles: Application to the Total Syntheses of (±)-Tuberostemospiroline and (±)-Stemona-lactam R
Junkai Fu, Hongjuan Shen, Yuanyuan Chang, Prof. Dr. Chuangchuang Li, Dr. Jianxian Gong and Prof. Dr. Zhen Yang*
• Highlighted in Org. Chem. Highlights, May, 11th, 2015.
A 4-substituted-1-tosyl-1,2,3-triazole-based stereoselective synthesis of structurally diverse oxaspirocycles is reported. The synthesis involves Rh-catalyzed loss of nitrogen from 4-substituted-1-tosyl-1,2,3-triazoles, Grignard reaction, and a ring-closing metathesis reaction as key steps. By employing readily available and stable 4-substituted-1-tosyl-1,2,3-triazoles as surrogates of diazo compounds and nitrogen sources, two types of oxaspirocycles were obtained. The latter compounds, which contain adjacent nitrogen stereocenters, could serve as the core structures of many natural products. This chemistry has been successfully applied to the total syntheses of (±)-tuberostemospiroline and (±)-stemona-lactam R.
83.Total Synthesis of Aplykurodinone-1
Gang Liu, Guangjian Mei, Runwen Chen, Haina Yuan, Zhen Yang*, and Chuang-chuang Li*
The concise total synthesis of aplykurodinone-1 with an unusual cis-fused hydrindane moiety has been accomplished without the need for any protecting group chemistry using a unique SmI2 mediated reductive cascade cyclization reaction and a direct cuprate mediated 1,4-addition. This work represents the first example of the use of a SmI2-mediated intramolecular cascade cyclization reaction between “halide, alkene and aldehyde” groups.
