Chemoenzymatic Preparation of Enantiopure Isomers of 4‐Aminochroman‐3‐ol and 1‐Amino‐1,2,3,4‐tetrahydronaphthalen‐2‐ol

• Published in: European Journal of Organic Chemistry
• Main Authors: Recuero, Verónica, de Gonzalo, Gonzalo, Brieva, Rosario, Gotor, Vicente
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2006
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/ejoc.200600385; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.200600385; https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.200600385

Abstract Enantiomerically pure N ‐protected cis ‐4‐aminochroman‐3‐ol (key precursor in the synthesis of novel HIV second‐generation protease inhibitors), its trans isomer and both cis ‐ and trans ‐1‐amino‐1,2,3,4‐tetrahydronaphthalen‐2‐ol, useful chiral catalysts in organic synthesis, have been successfully prepared through a lipase‐catalyzed kinetic acylation of the alcohol moiety, employing as substrates the corresponding N ‐benzyloxycarbonyl‐protected derivatives. Of the biocatalysts tested, Pseudomonas cepacea and Candida antarctica B lipases showed excellent enantioselectivities in the acylation processes depending on the reaction conditions employed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)