Counterion-Mediated Hydrogen-Bonding Effects: Mechanistic Study of Gold(I)-Catalyzed Enantioselective Hydroamination of Allenes

被引：39

作者：

Kim, Ji Hye ^{[1
]}

Park, Sung-Woo ^{[1
]}

Park, Sae Rom ^{[1
]}

Lee, Sungyul ^{[1
]}

Kang, Eun Joo ^{[1
]}

机构：

[1] Kyung Hee Univ, Dept Appl Chem, Yongin 446701, Gyeonggi Do, South Korea

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2011年 / 6卷 / 08期

关键词：

allenes; counterions; gold; hydrogen bonds; nucleophilic addition; CATALYZED INTRAMOLECULAR HYDROAMINATION; HOMOGENEOUS GOLD CATALYSIS; INTERMOLECULAR HYDROAMINATION; CATIONIC GOLD(I); ALPHA-AMINOALLENES; COMPLEXES; CYCLOISOMERIZATION; HYDROALKOXYLATION; ALKYNES; HYDROARYLATION;

D O I：

10.1002/asia.201100135

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two of a kind: A new type of counterion-mediated syn-addition mechanism has been presented in gold-catalyzed enantioselective hydroamination reactions with [(R)-binap(AuOPNB)2] (OPNB=para-nitrobenzoate). A combination of both hydrogen bonding and the N-Au interaction efficiently controlled the challenging enantioselectivity of allenes. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1982 / 1986

页数：5

共 13 条

[1] Mechanistic Study of Gold(I)-Catalyzed Intermolecular Hydroamination of Allenes
Wang, Z. Jane
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[2] Gold(I)-catalyzed enantioselective intramolecular hydroamination of allenes
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[3] Gold(I)-catalyzed enantioselective intramolecular hydroamination of allenes with ureas
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[4] Gold(I)-Catalyzed Stereoconvergent, Intermolecular Enantioselective Hydroamination of Allenes
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[5] Gold(I)-catalyzed dynamic kinetic enantioselective intramolecular hydroamination of allenes
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[8] Mechanistic Study of Gold(I)-Catalyzed Hydroamination of Alkynes: Outer or Inner Sphere Mechanism?
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[9] Assessing counterion effects in gold-catalyzed domino spirocyclization: an industrial perspective on hydrogen bonding
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[10] Chiral acyclic diaminocarbene gold complexes as catalysts for enantioselective intramolecular hydroamination of allenes: Systematic study of ligand substituent effects on enantioselectivities
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