Synthesis of Substituted (Rp)-2-Aminomethyl-1-[(S)-4-isopropyloxazolin-2-yl]ferrocenes

• Published in: European journal of organic chemistry Vol. 2002; no. 4; pp. 692 - 695
• Main Authors: Sebesta, R, Toma, S, Salisova, M
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag GmbH 01.02.2002; WILEY‐VCH Verlag GmbH; Wiley
• Subjects: Amines; Chemistry; Chemistry, Organic; Metallocenes; Nucleophilic substitution; Oxygen heterocycles; Physical Sciences; Planar chirality; Science & Technology; oxygen heterocycles; planar chirality; ASYMMETRIC CATALYSIS; FERROCENYL-OXAZOLINE; LIGANDS; nucleophilic substitution; amines; CATALYZED ALLYLIC SUBSTITUTION; DERIVATIVES; metallocenes
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/1099-0690(200202)2002:4<692::AID-EJOC692>3.0.CO;2-2

The synthesis of novel N‐substituted (Rp)‐2‐aminomethyl‐1‐[(S)‐4‐isopropyloxazolin‐2‐yl]ferrocenes is described. The usual synthesis by nucleophilic displacement of an acetoxy group with amine in methanol does not work in the case of the corresponding oxazolinylferrocene. This problem was solved by changing the leaving group to a pivaloyloxy group. Addition of water to the reaction media increases the yields and shortens the reaction times. We have also developed a new methodology for the direct conversion of the hydroxy group to an amine via an intermediate iodide.