Cyclopentane Formation from Flexible Precursors Using Samarium(II) Reagents
Publication Date
4-30-2018
Document Type
Article
Organizational Units
College of Natual Science and Mathematics, Chemistry and Biochemistry
Keywords
Samarium, Carbocycles, Alkylation, Aldol reactions, Cyclization
Abstract
This study presents three efficient methods for five‐membered ring carbocycle synthesis using samarium(II) reagents. Simple organic starting materials engage in intramolecular Reformatsky aldol, enolate alkylation, and pinacol cyclizations. A promising lead result has also been established demonstrating enantioselectivity in a chiral ligand controlled Reformatsky aldol reaction.
Three efficient methods for five‐membered ring carbocycle synthesis have been developed from simple starting materials using samarium(II) reagents. A Reformatsky aldol reaction proceeded efficiently with samarium(II) iodide using lithium bromide as an additive. A new intramolecular alkylation of a samarium enolate was realized with a pendant sulfonate ester leaving group. Pinacol cyclization of a simple diketone was also demonstrated giving a diol product in high stereoselectivity. A promising lead result has been established demonstrating enantioselectivity in a chiral ligand controlled Reformatsky aldol reaction.
Publication Statement
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Recommended Citation
Aretz, C. D., Escobedo, H., & Cowen, B. J. (2018). Cyclopentane Formation from Flexible Precursors Using Samarium(II) Reagents. European Journal of Organic Chemistry, 2018(16), 1880-1884. DOI: 10.1002/ejoc.201800102.