77629-16-4Relevant academic research and scientific papers
The conversion of carbonyl compounds into pentadienylamines by a Julia-Kocienski olefination procedure
Bastin, Reyhan,Liron, Mélanie,Taylor, Richard J. K.
scheme or table, p. 2183 - 2187 (2009/04/08)
Julia-Kocienski olefination has been successfully employed to convert carbonyl compounds into the corresponding Boc-protected 1,3-pentadienyl amines in a C4N homologation process. Good to excellent yields are achieved in THF using MHMDS as base to deprotonate the precursor 1-phenyl-1H-tetrazol-5- ylsulfone reagent. The nature of the metallic countercation dramatically affects the stereoselectivity of the newly formed alkene: good levels of 2E,4E-stereoselectivity are achieved using KHMDS whereas LiHMDS gives a predominance of the 2E,4Z-dienyl product. Georg Thieme Verlag Stuttgart.
Benzotriazole-Mediated Stereoselective Olefination of Carboxylic Esters: Transformation of α-Amino Acid Esters into Chiral Allylamines
Katritzky, Alan R.,Cheng, Dai,Li, Jianqing
, p. 3438 - 3444 (2007/10/03)
Diastereoselective trans-olefinations of carboxylic esters 3a-h have been accomplished using benzylic or allylic benzotriazole derivatives 1a-e to prepare α-(benzotriazol-1-yl) ketones 4a-i, for the subsequent reduction of 4a-i, and finally for low-valent titanium-effected dehydroxybenzotriazolylation.1 N-Protected α-amino acid esters 9a-c and 15 thus give allylamines 13a-e and 19 with virtually full retention of chirality. Mechanistic aspects of the dehydroxybenzotriazolylation are discussed.
Highly Stereoselective Route to (E)-Allyl Amines via Vinyltri-n-butylphosphonium Salts (Schweizer Reaction)
Meyers, A. I.,Lawson, Jon P.,Carver, David R.
, p. 3119 - 3123 (2007/10/02)
The reaction of vinyltri-n-butylphosphonium salts, aldehydes, and sodiophthalimide in THF gave good yields of the allylic phthalimides with high E stereoselectivity (75-100percent).The use of the vinyltriphenylphosphonium salts (Schweizer reaction) gave the allyl phthalimide with the Z isomer predominating.A study of the phthalimide cation and the effect of added lithium salt showed some reversal in the olefin geometry but in general the selectivity was only 3:1
