Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 17, Pages 11226-11239Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01310
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Funding
- Hungarian Scientific Research Fund [OTKA K 104528]
- National Research, Development and Innovation Office (NKFIH) [PD 128612]
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A general, scalable two-step regio- and diastereoselective method has been described for the synthesis of versatile alkaloid-type azetidines from simple building blocks with excellent overall yields. In the kinetically controlled reaction, only the formation of the strained four-membered ring can be achieved instead of the thermodynamically favorable five-membered rings under appropriate conditions. Remarkable functional group tolerance has also been demonstrated. In this paper, we give a new scope of Baldwin's rules by density functional theory (DFT) calculations with an explicit solvent model, confirming the proposed reaction mechanisms and the role of kinetic controls in the stereochemical outcome of the reported transition-metal-free carbon-carbon bond formation reactions.
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