Open AccessEnzymatic Approach to the Synthesis of Enantiomerically Pure Hydroxy Derivatives of 1,3,5-Triaza-7-phosphaadamantane
Author(s) -
Małgorzata Kwiatkowska,
Jarosław Błaszczyk,
Lesław Sieroń,
P. Kiełbasiński
Publication year - 2021
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.0c02586
Subject(s) - chemistry , hydroxymethyl , kinetic resolution , enantiomer , sulfide , aryl , hydrolysis , stereoselectivity , organic chemistry , decane , acetylation , enzyme , biocatalysis , enzymatic hydrolysis , stereochemistry , catalysis , enantioselective synthesis , reaction mechanism , alkyl , biochemistry , gene
A series of enantiomerically pure derivatives of 6-(1-hydroxyalkyl)-1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane 5 were successfully synthesized for the first time. A series of hydrolytic enzymes was applied in a stereoselective acetylation performed under kinetic resolution conditions. Although the secondary alcohols: α-aryl-hydroxymethyl-PTA (phosphines) 5b-d' , PTA-oxides 8b-d' , and PTA-sulfides 9b-d' were found to be totally unreactive in the presence of all the enzymes and various conditions applied, the primary alcohols, i.e., the hydroxymethyl derivatives PTA oxide 8a and PTA sulfide 9a , were successfully resolved into enantiomers with moderate to good enantioselectivity (up to 95%). The absolute configurations of the products were determined by an X-ray analysis and chemical correlation.