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Expanding Insight into Asymmetric Palladium‐Catalyzed Allylic Alkylation of N‐Heterocyclic Molecules and Cyclic Ketones
Author(s) -
Bennett Nathan B.,
Duquette Douglas C.,
Kim Jimin,
Liu WenBo,
Marziale Alexander N.,
Behenna Douglas C.,
Virgil Scott C.,
Stoltz Brian M.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300030
Subject(s) - chemistry , tsuji–trost reaction , library science , polymer science , allylic rearrangement , organic chemistry , catalysis , computer science
Eeny, meeny, miny … enaminones! Lactams and imides have been shown to consistently provide enantioselectivities substantially higher than other substrate classes previously investigated in the palladium‐catalyzed asymmetric decarboxylative allylic alkylation. Several new substrates have been designed to probe the contributions of electronic, steric, and stereoelectronic factors that distinguish the lactam/imide series as superior alkylation substrates (see scheme). These studies culminated in marked improvements on carbocyclic allylic alkylation substrates.