1,3-Amino alcohols from 4-amino-1-aza dienes. Diastereo- and enantioselective approach to the four diastereoisomers of the N-terminal amino acid component of nikkomycins B and BX

New 1,3-amino alcohols derived from enantiopure bridgehead β-aminobicyclo[2.2.2]oct-5-ene-2-carboxylic acids

“…They constitute convenient starting materials for the synthesis of various 1,3-heterocycles for example (Ager et al 1996;Fülöp et al 1997;Gyonfalvi et al 2003;Kivelä et al 2003Kivelä et al , 2005. Although 1,2-amino alcohols have received much attention because they are generally readily accessible in enantiomerically pure form from natural precursors (Gyonfalvi et al 2003;Reetz et al 1987;Delair et al 1994;Masui and Shiori 1998;Laczkowski et al 2009;, the synthesis and the use of chiral 1,3-amino alcohols are still undergoing development and remain a challenge (Lait et al 2007;Didier et al 1991; Barluenga et al 1993; Bartoli et al 1994;Kossenjans and Martens 1999;Kochi et al 2003;Raghavan et al 2004;Murai et al 2005;Balazs et al 2007). …”

1,3-Dicarbonyl compounds in stereoselective domino and multicomponent reactions

“…Among them, the CoCl 2 -catalyzed coupling between a 1,3-dicarbonyl compound 53, an aromatic aldehyde 54, and acetonitrile in the presence of acetyl chloride, 43 provides a general access to β-acetamido carbonyl compounds 55 (Scheme 19). These products are the building blocks of numerous pharmaceutical and biological compounds, and they can be used as precursors of 1,3-amino alcohols, 44 β-amino acids 43 and γ-lactams. A large number of catalysts have been reported for this reaction, with diastereomeric ratio ranging from 50/50 to 98/2.…”

One-pot three-component synthesis of β-acetamido carbonyl compounds catalyzed by heteropoly acids

“…b-Acetamido carbonyl compounds can be used as precursors of 1,3-amino alcohols, b-amino acids, and c-lactams [10][11][12][13]. Some of them also have shown biological and pharmaceutical properties and were used in the preparation of antibiotic drugs such as nikkomycin or neopolyoxins [14].…”