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Highly Stereoselective Diels-Alder Reactions Catalyzed by Diboronate Complexes.
Li, Yuan-He; Zhang, Su-Lei; Lu, Yong; Xiao, Bo; Sun, Tian-Yu; Xu, Qian-Qian; Chen, Jia-Hua; Yang, Zhen.
Afiliación
  • Li YH; Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Peking University, Beijing, 100871, China.
  • Zhang SL; Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Peking University, Beijing, 100871, China.
  • Lu Y; Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Peking University, Beijing, 100871, China.
  • Xiao B; Lab of Computational Chemistry and Drug Design, State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen, 518055, China.
  • Sun TY; Lab of Computational Chemistry and Drug Design, State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen, 518055, China.
  • Xu QQ; Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Peking University, Beijing, 100871, China.
  • Chen JH; Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Peking University, Beijing, 100871, China.
  • Yang Z; Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), Peking-Tsinghua Center for Life Sciences, Peking University, Beijing, 100871, China.
Angew Chem Int Ed Engl ; 62(33): e202303075, 2023 Aug 14.
Article en En | MEDLINE | ID: mdl-37202371
ABSTRACT
A highly enantioselective catalytic system for exo-Diels-Alder reactions was developed based on the newly discovered bispyrrolidine diboronates (BPDB). Activated by various Lewis or Brønsted acids, BPDB can catalyze highly stereoselective asymmetric exo-Diels-Alder reactions of monocarbonyl-based dienophiles. When 1,2-dicarbonyl-based dienophiles are used, the catalyst can sterically distinguish between the two binding sites, which leads to highly regioselective asymmetric Diels-Alder reactions. BPDB can be prepared as crystalline solids on a large scale and are stable under ambient condition. Single-crystal X-ray analysis of the structure for acid-activated BPDB indicated that its activation involves cleavage of a labile B←N bond.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2023 Tipo del documento: Article País de afiliación: China
Texto completo
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XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2023 Tipo del documento: Article País de afiliación: China