117553-99-8Relevant academic research and scientific papers
Diastereoselective tandem addition-cyclization reactions of unsaturated tertiary amines initiated by photochemical electron transfer (PET)
Bertrand,Hoffmann,Humbel,Pete
, p. 8690 - 8703 (2000)
Polycyclic molecules and tetrahydroquinoleines were obtained in a tandem reaction involving the diastereoselective addition of α-aminoalkyl radicals to (5R)-5-menthyloxy-2[5H]-furanone 1. The facial diastereoselectivity on 1 is ≥90%. The α-aminoalkyl radicals were produced from tertiary amines by photochemical-induced electron transfer. When N, N-dialkylanilines 19 were used as starting tertiary amines, a rearomatization step was involved and important side reactions of 1 were observed. A mechanistic study involving isotopic labeling of the starting amine indicated that the byproducts resulted from reduction of I during the rearomatization process. An efficient optimization of the reaction was obtained by simply adding acetone or cyclopentanone as mild oxidants to the reaction mixture. The side products resulting from reduction of the furanone 1 were completely suppressed under these conditions, and the yields of the tetrahydroquinolines 21ai, 22a-f, and 26g-i were doubled.
Highly efficient and stereoselective radical addition of tertiary amines to electron-deficient alkenes - Application to the enantioselective synthesis of necine bases
Bertrand, Samuel,Hoffmann, Norbert,Pete, Jean-Pierre
, p. 2227 - 2238 (2007/10/03)
A convenient and highly efficient method for the regio- and stereoselective addition of tertiary amines to electron-deficient alkenes has been elaborated. It is based on a radical chain reaction of α-aminyl radicals with alkenes, induced by a photoelectro
ASYMMETRIC 1,4-ADDITIONS TO 5-ALKOXY-2(5H)-FURANONES ENANTIOSELECTIVE SYNTHESIS AND ABSOLUTE CONFIGURATION DETERMINATION OF β-AMINO-γ-BUTYROLACTONES AND AMINO DIOLS
Lange, B. de,Bolhuis, F. van,Feringa, Ben L.
, p. 6799 - 6818 (2007/10/02)
The synthesis of enantiomerically pure β-amino-γ-butyrolactones via asymmetric conjugate addition of various amines to 5-methyloxy-2(5H)-furanone is described.This route provides access to new multifunctional homochiral building blocks.The absolute configuration of the β-amino-γ-butyrolactones is established by X-ray analysis and 1H NMR correlation.The conjugate addition of amines to 2(5H)-furanone, 5-alkyl-2(5H)-furanones and 5-alkoxy-2(5H)-furanones was studied and an enhanced reactivity was observed in 2(5H)-furanones due to a γ-alkoxy-effect.The synthetic utility of the asymmetric amine addition is illustrated in an efficient route to various optically pure 2-amino-1,4-butanediols.
ASYMMETRIC SYNTHESIS OF 2-AMINO-1,4-DIOLS
Feringa, Ben L.,Lange, B. de
, p. 1303 - 1306 (2007/10/02)
Diastereoselective addition of amines to (l)-5-menthyloxy-2-(5H)-furanone yields aminolactones that upon reduction with LiAlH4 provide enantiomerically pure aminodiols.
