Tetrahedron

Kinetic resolution of primary amines via enantioselective N-acylation with acyl chlorides in the presence of supramolecular cyclodextrin nanocapsules

H Asahara, T Kida, T Iwamoto, T Hinoue, M Akashi

Index: Asahara, Haruyasu; Kida, Toshiyuki; Iwamoto, Takuya; Hinoue, Tomoaki; Akashi, Mitsuru Tetrahedron, 2014 , vol. 70, # 2 p. 197 - 203

Full Text: HTML

Citation Number: 2

Abstract

Abstract The non-enzymatic kinetic resolution of primary amines via enantioselective N- acylation with acyl chlorides was accomplished for the first time by using the selective sequestration of one enantiomer within a supramolecular cyclodextrin (CD) nanocapsule in nonpolar solvents. In addition, the first example of a crystalline structure for an inclusion complex between an acyl chloride and a CD derivative is reported.

Related Articles:

Highly efficient resolutions with isopropylidene glycerol 3-carboxy-2-naphthoate

[Pallavicini, Marco; Bolchi, Cristiano; Fumagalli, Laura; Valoti, Ermanno; Villa, Luigi Tetrahedron Asymmetry, 2002 , vol. 13, # 20 p. 2277 - 2282]

1, 2-vs. 1, 4-addition of nucleophilic organometallics to nonracemic 2-(1-naphthyl)-and 2-cinnamyl-1, 3-oxazolidines

[Pridgen, Lendon N.; Mokhallalati, Mohamed K.; Wu, Ming-Jung Journal of Organic Chemistry, 1992 , vol. 57, # 4 p. 1237 - 1241]

Highly Enantioselective Hydrogen??Transfer Reductive Amination: Catalytic Asymmetric Synthesis of Primary Amines

[Kadyrov, Renat; Riermeier, Thomas H. Angewandte Chemie - International Edition, 2003 , vol. 42, # 44 p. 5472 - 5474]

Palladium Catalysts on Alkaline??Earth Supports for Racemization and Dynamic Kinetic Resolution of Benzylic Amines

[Parvulescu, Andrei N.; Jacobs, Pierre A.; De Vos, Dirk E. Chemistry - A European Journal, 2007 , vol. 13, # 7 p. 2034 - 2043]

Asymmetric Synthesis of Nonracemic Primary Amines via Spiroborate-Catalyzed Reduction of Pure (E)-and (Z)-O-Benzyloximes: Applications toward the Synthesis of …

[Ou, Wenhua; Espinosa, Sandraliz; Melendez, Hector J.; Farre, Silvia M.; Alvarez, Jaime L.; Torres, Valerie; Martinez, Ileanne; Santiago, Kiara M.; Ortiz-Marciales, Margarita Journal of Organic Chemistry, 2013 , vol. 78, # 11 p. 5314 - 5327]

More Articles...