1607830-30-7Relevant articles and documents
Kirmse–Doyle- and Stevens-Type Rearrangements of Glutarate-Derived Oxonium Ylides
Skrobo, Benedikt,Schl?rer, Nils E.,Neud?rfl, J?rg -M.,Deska, Jan
, p. 3209 - 3217 (2018)
A novel chemoenzymatic synthetic cascade enables the preparation of densely decorated tetrahydrofuran building blocks. Here, the lipase-catalyzed desymmetrization of 3-alkoxyglutarates renders highly enantioenriched carboxylic acid intermediates, whose subsequent activation and oxonium ylide rearrangement by means of rhodium or copper complexes furnishes functionalized O-heterocycles with excellent diastereoselectivity. The two-step protocol offers a streamlined and flexible synthesis of tetrahydrofuranones bearing different benzylic, allylic or allenylic side chains with full control over multiple stereogenic centers.
Synthesis of GABOB and GABOB-Based Chiral Units Possessing Distinct Protecting Groups
Ivic, Trpimir,Dokli, Irena,Rimac, Ana,Hamerak, Zdenko
, p. 631 - 638 (2015/10/05)
In addition to the varied biological activity of GABOB (4-amino-3-hydroxybutanoic acid), the structure of its protected derivatives makes them interesting chiral intermediates for the synthesis of more complex compounds. A stereoselective route to GABOB derivatives with three different protecting groups is presented, using anhydride desymmetrization as a chirality-inducing step. Selective removal of the protecting groups gave compounds with a free carboxylic acid or hydroxy group. Removal of all of the protecting groups allowed GABOB to be isolated in good yield and with excellent ee.
