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Design and Asymmetric Control of Orientational Chirality by Using the Combination of C(sp2)-C(sp) Levers and Achiral N-Protecting Group.
Wang, Yu; Xu, Ting; Jin, Shengzhou; Wang, Jia-Yin; Yuan, Qingkai; Liu, Hao; Tang, Yao; Zhang, Sai; Yan, Wenxin; Jiao, Yinchun; Li, Guigen.
Affiliation
  • Wang Y; School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.
  • Xu T; School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.
  • Jin S; School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.
  • Wang JY; School of Pharmacy, Continuous Flow Engineering Laboratory of National Petroleum and Chemical Industry, Changzhou University, Changzhou, Jiangsu, 213164, China.
  • Yuan Q; Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, 79409-1061, USA.
  • Liu H; Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, 79409-1061, USA.
  • Tang Y; Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, 79409-1061, USA.
  • Zhang S; Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, 79409-1061, USA.
  • Yan W; School of Pharmacy, Continuous Flow Engineering Laboratory of National Petroleum and Chemical Industry, Changzhou University, Changzhou, Jiangsu, 213164, China.
  • Jiao Y; School of Chemistry and Chemical Engineering, Key Laboratory of Theoretical Organic Chemistry and Functional Molecular, Ministry of Education, Hunan University of Science and Technology, Xiangtan, 411201, China.
  • Li G; School of Chemistry and Chemical Engineering, Key Laboratory of Theoretical Organic Chemistry and Functional Molecular, Ministry of Education, Hunan University of Science and Technology, Xiangtan, 411201, China.
Chemistry ; 30(28): e202400005, 2024 May 17.
Article in En | MEDLINE | ID: mdl-38497560
ABSTRACT
New chiral targets of orientational chirality have been designed and asymmetrically synthesized by taking advantage of N-sulfinyl imine-directed nucleophilic addition/oxidation, Suzuki-Miyaura, and Sonogashira cross-coupling reactions. Orientation of single isomers has been selectively controlled by using aryl/alkynyl levers [C(sp2)-C(sp) axis] and tBuSO2- protecting group on nitrogen as proven by X-ray diffraction analysis. The key structural characteristic of resulting orientational products is shown by remote through-space blocking manner. Seventeen examples of multi-step synthesis were obtained with modest to good chemical yields and complete orientational selectivity.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Chemistry Journal subject: QUIMICA Year: 2024 Type: Article Affiliation country: China
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PubMed Links
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Chemistry Journal subject: QUIMICA Year: 2024 Type: Article Affiliation country: China