(1S,2S)-1-Amino-2-hydroxy-1,2,3,4-tetrahydronaphthalene: a new chiral auxiliary for asymmetric Reformatsky reactions

Pentafluorophenyl carbonyl compounds in the Reformatsky-type reactions promoted with Fe(CO)5-based metal complex systems

“…are assigned to Zaitsev-Barbier-Reformatsky reactions [1][2][3][4][5]. Various metals are involved in these reactions such as zinc [4], magnesium [6] and more recently samarium [7], silicon [8], indium [5], etc. Although the common conditions for above reactions are continuously being improved, certain difficulties exist for carrying out them such as the need to use anhydrous and volatile solvents and inert atmosphere, low temperatures, heterogeneous medium, effective agitating and activating a metal surface.…”

“…Most metal complexes widely used in the organic synthesis are either expensive or not easily available [5,7,10]. On the other hand, iron oxides, salts and complexes are cheap and recently they have been proposed as catalysts and promoters for organic synthesis [15][16][17][18][19], at the same time the available metal carbonyls are used as reagents much more rarely [20].…”

Chemoenzymatic Preparation of Enantiopure Isomers of 4‐Aminochroman‐3‐ol and 1‐Amino‐1,2,3,4‐tetrahydronaphthalen‐2‐ol

“…The most important applications of these compounds include the enantioselective addition of Et 2 Zn to aldehydes,9 the Diels–Alder reaction10 and the enantioselective reduction of prochiral ketones with BH 3 · SMe 2 11. (1 R ,2 S )‐1‐Amino‐1,2,3,4‐tetrahydronaphthalen‐2‐ol has recently been synthesized and applied to this last reaction12 and the (1 S ,2 S ) enantiomer has been described as a chiral auxiliary in Reformatsky‐type reactions 13…”

Katalytische enantioselektive Reformatsky‐Reaktionen mit Aldehyden

“…Asymmetrische Varianten der Reformatsky-Reaktion nutzen chirale Auxiliare [4] oder Liganden. [5] Kürzlich berichtete Cozzi über katalytische enantioselektive Umsetzungen mit Ketonen und Iminen als Elektrophilen.…”