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

✍ Scribed by Verónica Recuero; Gonzalo de Gonzalo; Rosario Brieva; Vicente Gotor

• Book ID: 102178569
• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 131 KB
• Volume: 2006
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200600385

✦ Synopsis

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)