Expanding Insight into Asymmetric Palladium-Catalyzed Allylic Alkylation of N-Heterocyclic Molecules and Cyclic Ketones

被引：41

作者：

Bennett, Nathan B. ^{[1
]}

Duquette, Douglas C. ^{[1
]}

Kim, Jimin ^{[1
]}

Liu, Wen-Bo ^{[1
]}

Marziale, Alexander N. ^{[1
]}

Behenna, Douglas C. ^{[1
]}

Virgil, Scott C. ^{[1
]}

Stoltz, Brian M. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 14期

基金：

美国国家科学基金会;

关键词：

allylation; asymmetric catalysis; heterocyclic compounds; high-throughput screening; palladium; ENANTIOSELECTIVE TSUJI ALLYLATION; PHOSPHINITE-OXAZOLINE LIGANDS; QUATERNARY STEREOCENTERS; ENOL CARBONATES; DECARBOXYLATIVE ALLYLATION; INNER-SPHERE; HAMIGERAN-B; HYDROGENATION; CONSTRUCTION;

D O I：

10.1002/chem.201300030

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Eeny, meeny, miny.ï̧ 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. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4414 / 4418

页数：5

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