20.500.12556/RUL-141984 Catalytic stereoconvergent synthesis of homochiral β‑CF$_3$, β‑SCF$_3$, and β‑OCF$_3$ benzylic alcohols We describe an efficient catalytic strategy for enantio- and diastereoselective synthesis of homochiral β-CF$_3$, β-SCF$_3$, and β-OCF$_3$ benzylic alcohols. The approach is based on dynamic kinetic resolution (DKR) with Noyori−Ikariya asymmetric transfer hydrogenation leading to simultaneous construction of two contiguous stereogenic centers with up to 99.9% ee, up to 99.9:0.1 dr, and up to 99% isolated yield. The origin of the stereoselectivity and racemization mechanism of DKR is rationalized by density functional theory calculations. Applicability of the previously inaccessible chiral fluorinated alcohols obtained by this method in two directions is further demonstrated: As building blocks for pharmaceuticals, illustrated by the synthesis of heat shock protein 90 inhibitor with in vitro anticancer activity, and in particular, needle-shaped crystals of representative stereopure products that exhibit either elastic or plastic flexibility, which opens the door to functional materials based on mechanically responsive chiral molecular crystals. adaptive crystals asymmetric catalysis density functional calculations drug design fluorine hydrogenation kinetic resolution ruthenium alcohols catalysts crystals ketones stereoselectivity true false true Angleški jezik Ni določen Članek v reviji 2022-10-13 13:16:06 2022-10-13 13:16:07 2022-11-09 03:54:41 0000-00-00 00:00:00 2022 0 0 Str. 396−404 iss. 5 Vol. 2 2022 0000-00-00 Zaloznikova Objavljeno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 54 2694-247X 10.1021/acsorginorgau.2c00019 111499267 acsorginorgau.2c00019.pdf acsorginorgau.2c00019.pdf 1 5EE7A03A4001BF26A1387E5D75BBDEAB bc22b28f4afec656f982c565fe7c76a1be7cac537c2cc88181374a400e2310ea 5679d428-5f39-11ed-9c94-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=163808 https://pubs.acs.org/doi/10.1021/acsorginorgau.2c00019 0 d3a2687a-4ae8-11ed-9c94-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=163217 Fakulteta za farmacijo 0 0 0