First enantioselective catalyst for the rearrangement of allylic imidates to allylic amides

M Calter, TK Hollis, LE Overman, J Ziller…

Index: Calter, Michael; Hollis, T. Keith; Overman, Larry E.; Ziller, Joseph; Zipp, G. Greg Journal of Organic Chemistry, 1997 , vol. 62, # 5 p. 1449 - 1456

Full Text: HTML

Citation Number: 156

Abstract

A series of Pd (II) complexes containing chiral diamine ligands were investigated as asymmetric catalysts for the rearrangement of allylic imidates to allyl amides. The best catalysts were cations obtained by dechlorination of dichloro [(S)-2-(isoindolinylmethyl)-N- methylpyrrolidine] palladium (II)(17) with silver salts in CH2Cl2. Catalyst 18 was studied thoroughly and shown by 1H NMR and X-ray crystallography analysis to be a C 1 ...

Related Articles:

Copper catalyzed N-arylation between aryl halides and nitriles in water: an efficient tandem synthesis of benzanilides

[Wang, Jichao; Yin, Xinchi; Wu, Jun; Wu, Datong; Pan, Yuanjiang Tetrahedron, 2013 , vol. 69, # 48 p. 10463 - 10469]

Efficient Manganese/Copper Bimetallic Catalyst for N??Arylation of Amides and Sulfonamides Under Mild Conditions in Water

[Teo, Yong-Chua; Yong, Fui-Fong; Ithnin, Idzham Khalid; Yio, Siew-Hui Trionna; Lin, Zhiyin European Journal of Organic Chemistry, 2013 , # 3 p. 515 - 524]

BippyPhos: A single ligand with unprecedented scope in the Buchwald–Hartwig amination of (hetero) aryl chlorides

[Crawford, Sarah M.; Lavery, Christopher B.; Stradiotto, Mark Chemistry - A European Journal, 2013 , vol. 19, # 49 p. 16760 - 16771]

A Novel Domino Synthesis of Quinazolinediones by Palladium??Catalyzed Double Carbonylation

[Li, Haoquan; Neumann, Helfried; Beller, Matthias; Wu, Xiao-Feng Angewandte Chemie - International Edition, 2014 , vol. 53, # 12 p. 3183 - 3186 Angew. Chem., 2014 , vol. 126, # 12 p. 3247 - 3250,4]

Bis (cyclopentadienyldicarbonyliron) as a Convenient Carbon Monoxide Source in Palladium-catalyzed Carbonylative Coupling of Aryl Iodides with Amines, Alcohols, …

[Nakaya, Ryotaro; Yorimitsu, Hideki; Oshima, Koichiro Chemistry Letters, 2011 , vol. 40, # 9 p. 904 - 906]

More Articles...