Asymmetric Synthesis of Dihydropyranones via Gold(I)-Catalyzed Intermolecular [4+2] Annulation of Propiolates and Alkenes
- Authors
- Kim, Hanbyul; Choi, Su Yeon; Shin, Seunghoon
- Issue Date
- Oct-2018
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- anionic surfactants; asymmetric gold catalysis; entropy control; intermolecular alkyne activation; alpha, beta-unsaturated delta-lactones
- Citation
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.57, no.40, pp.13130 - 13134
- Indexed
- SCIE
SCOPUS
- Journal Title
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Volume
- 57
- Number
- 40
- Start Page
- 13130
- End Page
- 13134
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/149264
- DOI
- 10.1002/anie.201807514
- ISSN
- 1433-7851
- Abstract
- Intermolecular asymmetric gold catalysis involving alkyne activation presents a significant challenge due to its distinct mechanistic mode from other metals. Herein, we report a highly enantioselective synthesis of alpha, beta-unsaturated delta-lactones from [4+2] annulation of propiolates and alkenes in upto 95% ee. Notably, for the desired chiral recognition, the choice of 1,1,2,2-tetrachloroethane as solvent was found to be crucial. Furthermore, an anionic surfactant (sodium dodecyl sulfate) improved the product selectivity in the divergence of the cyclopropyl gold carbene intermediate.
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