An enantioselective synthesis of (−)-slaframine

The Chemistry of Vicinal Diamines

“…Nucleophilic displacements of tosylates or mesylates are also frequently employed, as in the synthesis of (À)-slaframine, [92] in the synthesis of (R)-and (S)-2,3-diaminopropanol from l-and d-serine, [93] or in the synthesis of (3R,4R)-and (3R,4S)-b,g-diamino acids from d-phenylalanine. [94] Several protected, chiral triamines and diamines were synthesized by Kokotos et al [95] For example, the Cbz-protected 4,5-diaminopentanoic acid 173 was prepared from the glutamic acid derivative 170 through a sequence involving the nucleophilic displacement of a mesyl group by sodium azide (Scheme 44).…”

Diastereoselectivity Switch in the Pd(0)/InI-Mediated Reactions of β-Lactams with Aldehydes: An Entry into Nonracemic Semiprotected (3E)-2,6-Enediols

“…Importantly, the application of azetidin-2-one 39 with the C3 phthalimide-protected amino group delivered the expected (3 E )-2,6- anti- amino alcohol 47 in moderate 54% yield and with good 86:14 2,6-anti-diastereoselectivity. This result exhibits the potential of the method in the asymmetric synthesis of this type of organic features difficult to prepare in another manner (Scheme , structure 47 ) …”

Die Chemie vicinaler Diamine

“…Diese Methode sollte auf die Herstellung anderer enantiomerenreiner Diamine übertragen werden können, vorausgesetzt die erforderlichen Alkene enthalten keine mit Osmiumtetroxid unvereinbaren funktionellen Gruppen. [92] b) (R)-und (S)-2,3-Diaminopropanol aus l-und d-Serin [93] und c) (3R,4R)-und (3R,4S)-b,g-Diaminosäuren aus d-Phenylalanin. [94] Einige geschützte chirale Triund Diamine wurden von Kokotos et al synthetisiert.…”