N1-Functionalized Indole-Phosphane Oxazoline (IndPHOX) Ligands in Asymmetric Allylic Substitution Reactions

被引：14

作者：

Wang, Yu ^{[1
]}

Vaismaa, Matti J. P. ^{[1
]}

Rissanen, Kari ^{[2
]}

Franzen, Robert ^{[1
]}

机构：

[1] Tampere Univ Technol, Dept Chem & Bioengn, FIN-33101 Tampere, Finland

[2] Univ Jyvaskyla, Dept Chem, Nanosci Ctr, Jyvaskyla 40014, Finland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 08期

基金：

芬兰科学院;

关键词：

Nitrogen heterocycles; Allylic compounds; Enantioselectivity; Amination; Alkylation; Palladium; CATALYZED N-ARYLATION; COUPLING REACTIONS; ARYL HALIDES; EFFICIENT; FUNCTIONALIZATION; VINYLATION; AZOLES;

D O I：

10.1002/ejoc.201101540

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Functionalized IndPHOX ligands bearing various groups have been synthesized and the effects of the N-1-substituent on the reaction rate, yield, and asymmetric induction in a palladium-catalyzed allylic substitution reaction are reported. The presence of an oxygen atom in the ligands, namely an N-MOM or N-THP group, led to enhancement of the enantioselectivity in the allylic amination reaction. In addition, a ligand with a chiral oxazoline ring at C-1 and a phosphane substituent at C-2 provided high enantioselectivity in good yield in an asymmetric allylic alkylation reaction.

引用

页码：1569 / 1576

页数：8

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