Asymmetric synthesis of acyclic amines through Zr- and Hf-catalyzed enantioselective alkylzinc reagents to Imines

被引：37

作者：

Akullian, LC ^{[1
]}

Porter, JR ^{[1
]}

Traverse, JE ^{[1
]}

Snapper, ML ^{[1
]}

Hoveyda, AH ^{[1
]}

机构：

[1] Boston Coll, Dept Chem, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2005年 / 347卷 / 2-3期

关键词：

asymmetric alkylation; asymmetric catalysis; chiral amines; hafnium; imines; zirconium;

D O I：

10.1002/adsc.200404319

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Readily available chiral amino acid-based ligands are used in metal-catalyzed additions of alkyl-zinc reagents to various aromatic and aliphatic imines; the desired amine products are formed efficiently and in high levels of optical purity. In cases where the more Lewis acidic Zr salts afford lower efficiency, Hf-based catalysts deliver significantly higher yields with similar enantioselectivities. Critical structural features of the N-activating groups as well as the optimal chiral ligands are discussed. A mechanistic working model is presented to rationalize the existing data and to serve as a predictive tool.

引用

页码：417 / 425

页数：9

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