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Utilizing Vinylcyclopropane Reactivity: Palladium‐Catalyzed Asymmetric [5+2] Dipolar Cycloadditions.
- Source :
- Angewandte Chemie; 9/28/2020, Vol. 132 Issue 40, p17582-17587, 6p
- Publication Year :
- 2020
-
Abstract
- Vinylcyclopropanes (VCPs) are commonly used in transition‐metal‐catalyzed cycloadditions, and the utilization of their recently realized reactivities to construct new cyclic architectures is of great significance in modern synthetic chemistry. Herein, a palladium‐catalyzed, visible‐light‐driven, asymmetric [5+2] cycloaddition of VCPs with α‐diazoketones is accomplished by switching the reactivity of the Pd‐containing dipolar intermediate from an all‐carbon 1,3‐dipole to an oxo‐1,5‐dipole. Enantioenriched seven‐membered lactones were produced with good reaction efficiencies and selectivities (23 examples, 52–92 % yields with up to 99:1 er and 12.5:1 dr). In addition, computational investigations were performed to rationalize the observed high chemo‐ and periselectivities. [ABSTRACT FROM AUTHOR]
- Subjects :
- VINYLCYCLOPROPANES
RING formation (Chemistry)
LACTONES
PALLADIUM
CHEMISTRY
KETENES
Subjects
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 132
- Issue :
- 40
- Database :
- Complementary Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 145990148
- Full Text :
- https://doi.org/10.1002/ange.202006366