Highly efficient biocatalytic resolution of cis- and trans-3-aminoindan-1-ol: syntheses of enantiopure orthogonally protected cis- and trans-indane-1,3-diamine.
The efficient chemoenzymatic synthesis of enantiopure 1,3-difunctionalized indane derivatives has been achieved. The corresponding cis and trans N-protected amino alcohols were successfully resolved by acetylation using lipase B, which is a biocatalyst isolated from Candida antarctica. All the possible isomers were obtained in very good chemical yields and ee values (>99 %). The utility of these compounds was subsequently shown by the preparation of orthogonally protected cis- and trans-indane-1,3-diamine using a Mitsunobu reaction. Both enantiomers of the trans isomer and a desymmetrized cis diastereomer were prepared in enantiopure form. Complete inversion of configuration during the Mitsunobu reaction was demonstrated by a combination of NMR techniques and molecular modeling. The utility and versatility of the strategy was also demonstrated by the selective deprotection of each nitrogen atom under mild reaction conditions.
López-García
Mónica
M
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Oviedo, Spain.
Alfonso
Ignacio
I
Gotor
Vicente
V
D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D003959:Diamines / Q000138:chemical synthesis* / Q000737:chemistry; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry; D008049:Lipase / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D013237:Stereoisomerism
D000605:Amino Alcohols; D003959:Diamines; D007189:Indans; D008049:Lipase; C093582:indan