Addition Reactions of Chloro-or Iodomethyllithium to Imines. Synthesis of Enantiopure Aziridines and β-Chloroamines

JM Concellón, H Rodríguez-Solla…

Index: Barluenga, Jose; Fernandez-Simon, Jose L.; Concellon, Jose M.; Yus, Miguel Synthesis, 1987 , # 6 p. 584 - 586

Full Text: HTML

Citation Number: 33

Abstract

We report a novel, simple, and efficient synthesis of aziridines and 1-chloroalkan-2-amines by the reaction of imines derived from various aldehydes and p-toluenesulfonamide or benzenesulfonamide with iodo-or chloromethyllithium, respectively. Both halogenated

Related Articles:

Reaction of trimethysilyl enol ethers with Simmons-Smith reagent. Facile synthesis of trimethylsilyl cyclopropyl ethers and cyclopropanols

[Rubottom,G.M.; Lopez,M.I. Journal of Organic Chemistry, 1973 , vol. 38, # 11 p. 2097 - 2099]

Yttrium-Mediated Conversion of Vinyl Grignard Reagent to a 1, 2-Dimetalated Ethane and Its Synthetic Application

[Tanaka, Ryoichi; Sanjiki, Hiroaki; Urabe, Hirokazu Journal of the American Chemical Society, 2008 , vol. 130, # 10 p. 2904 - 2905]

Exploiting the enantioselectivity of Baeyer-Villiger monooxygenases via boron oxidation

[Brondani, Patricia B.; Dudek, Hanna; Reis, Joel S.; Fraaije, Marco W.; Andrade, Leandro H. Tetrahedron Asymmetry, 2012 , vol. 23, # 9 p. 703 - 708]

Highly Selective Reaction of α-Halo-α, β-unsaturated Esters with Ketones or Aldehydes Promoted by SmI2: An Efficient Alternative Access to Baylis-Hillman Adducts

[Imamoto, Tsuneo; Hatajima, Toshihiko; Takiyama, Nobuyuki; Takeyama, Toshiaki; Kamiya, Yasuo; Yoshizawa, Takeshi Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 12 p. 3127 - 3135]

Highly Selective Reaction of α-Halo-α, β-unsaturated Esters with Ketones or Aldehydes Promoted by SmI2: An Efficient Alternative Access to Baylis-Hillman Adducts

[Imamoto, Tsuneo; Hatajima, Toshihiko; Takiyama, Nobuyuki; Takeyama, Toshiaki; Kamiya, Yasuo; Yoshizawa, Takeshi Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991 , # 12 p. 3127 - 3135]

More Articles...