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Cyclopentane Formation from Flexible Precursors Using Samarium(II) Reagents
Author(s) -
Aretz Christopher D.,
Escobedo Humberto,
Cowen Bryan J.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800102
Subject(s) - chemistry , samarium , aldol reaction , alkylation , reagent , reformatsky reaction , pinacol , diol , trifluoromethanesulfonate , stereoselectivity , cyclopropanation , medicinal chemistry , organic chemistry , catalysis
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.