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Asymmetric Hydrogenation of Racemic Allylic Alcohols via an Isomerization-Dynamic Kinetic Resolution Cascade.
Wang, Kun; Niu, Saisai; Guo, Xin; Tang, Weijun; Xue, Dong; Xiao, Jianliang; Sun, Huaming; Wang, Chao.
Afiliação
  • Wang K; Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.
  • Niu S; Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.
  • Guo X; Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.
  • Tang W; Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.
  • Xue D; Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.
  • Xiao J; Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, U.K.
  • Sun H; Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.
  • Wang C; Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.
J Org Chem ; 87(5): 3804-3809, 2022 03 04.
Article em En | MEDLINE | ID: mdl-35041421
ABSTRACT
Prochiral racemic allylic alcohols are converted to enantioenriched chiral alcohols bearing adjacent stereocenters catalyzed by a diamine diphosphine Ru complex in the presence of tBuOK. The protocol features a broad substrate scope (56 examples) and high diastereo- and enantioselectivities (up to >991 dr, >99% ee) and could be applied to the synthesis of enantioenriched chromane and indane compounds. Mechanistic studies suggest that the reaction proceeds via tBuOK-promoted allylic alcohol isomerization followed by Ru-catalyzed hydrogenative dynamic kinetic resolution.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Álcoois Idioma: En Ano de publicação: 2022 Tipo de documento: Article
Texto completo
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Álcoois Idioma: En Ano de publicação: 2022 Tipo de documento: Article