Highly Efficient Biocatalytic Resolution of cis‐ and trans‐3‐Aminoindan‐1‐ol: Syntheses of Enantiopure Orthogonally Protected cis‐ and trans‐Indane‐1,3‐diamine

• Published in: Chemistry – A European Journal
• Main Authors: López‐García, Mónica, Alfonso, Ignacio, Gotor, Vicente
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2004
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/chem.200306070; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.200306070; https://onlinelibrary.wiley.com/doi/full/10.1002/chem.200306070

Abstract 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.