Synthesis and use of a phosphoramidite ligand for the copper-catalyzed enantioselective allylic substitution. Tandem allylic substitution/ring-closing metathesis

被引：58

作者：

Tissot-Croset, K ^{[1
]}

Polet, D ^{[1
]}

Gille, S ^{[1
]}

Hawner, C ^{[1
]}

Alexakis, A ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

来源：

SYNTHESIS-STUTTGART | 2004年 / 15期

关键词：

allylic substitution; copper catalysis; ruthenium catalysis; enantioselectivity; Grignard reagents;

D O I：

10.1055/s-2004-829188

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new one-pot method of reductive amination is used to prepare a chiral C2 symmetrical amine. This amine is used for the synthesis of a new chiral phosphoramidite ligand. The new ligand is, in turn, used to illustrate the enantioselective copper-catalyzed allylic substitution with Grignard reagents. When a remote double bond is located on the Grignard reagent, the newly formed alkene undergoes an in situ ruthenium-catalyzed ring-closing metathesis to afford the cyclized product in 77% yield and 94% ee.

引用

页码：2586 / 2590

页数：5

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