Vanadium(II)‐ und Niob(III)‐induzierte, diastereoselektive Pinakol‐Kupplung homochiraler Peptidaldehyde zu C₂‐symmetrischen HIV‐Protease‐Inhibitoren

Abstract

Im Kilogramm‐Maßstab können potente Inhibitoren der HIV‐Protease wie 1 durch diastereoselektive, reduktive Dimerisierung homochiraler Peptidaldehyde hergestellt werden. Möglich wird dies durch den Einsatz von Niob‐oder in situ erzeugten Vanadium‐Katalysatoren im entscheidenden Reaktionsschritt, Aryl = 1‐Naphthyl.magnified image

Chromium‐Catalyzed Pinacol‐Type Cross‐Coupling: Studies on Stereoselectivity

“…1,2-Diols can be generated in general by bishydroxylation of olefinic double bonds [1] or by reductive coupling of carbonyl compounds. [2] The latter method plays an important role in the synthesis of HIV-protease inhibitors [3] and of natural products [4] such as taxol [5] and cotylenol [6] and their derivatives. For their synthesis this reaction has to be performed in a diastereoselective fashion.…”

Diastereoselective Ce(OiPr)3-Catalyzed Pinacol Couplings of Aldehydes

“…Substances which are sensitive against moisture and air were stored in a glove box. Ce(OiPr) 3 was synthesized according to the procedure described in ref. [15].…”

“…[2] The latter method plays an important part in the synthesis of HIV-protease inhibitors [3] and natural products such as taxol.…”

Pinacol Coupling of Aromatic Aldehydes and Ketones by TiCl4–Mg–THF Under Ultrasound Irradiation

“…1 Several approaches to their syntheses have been described. Pinacol coupling reactions constitute one of the most straight forward methods.…”