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Expanding insight into asymmetric palladium-catalyzed allylic alkylation of N-heterocyclic molecules and cyclic ketones.

ABSTRACT: 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.

SUBMITTER: Bennett NB

PROVIDER: S-EPMC3815597 | biostudies-literature | 2013 Apr

REPOSITORIES: biostudies-literature

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Expanding insight into asymmetric palladium-catalyzed allylic alkylation of N-heterocyclic molecules and cyclic ketones.

Bennett Nathan B NB Duquette Douglas C DC Kim Jimin J Liu Wen-Bo WB Marziale Alexander N AN Behenna Douglas C DC Virgil Scott C SC Stoltz Brian M BM

Chemistry (Weinheim an der Bergstrasse, Germany) 20130227 14

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 ...[more]

PMID: 23447555

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