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Nine 1,3-dichlorobenzene congeners were selected as model compds. to assess the relative rates of proton abstraction from 4- and 5-positions ("ortho" vs. "meta" metalation). Using lithium 2,2,6,6-tetramethylpiperidide as the basic reagent, the chlorine-adj ...
The relative displacement rates of the halide substituent from 2-fluoro- and 2-chloropyridines by EtONa in EtOH at +25 Deg were assessed by competition kinetics. The 2-fluoropyridine reacts 320 times faster than the chloro analog. A CF3 group increases the ...
The title cyclophanes, such as I, were prepd. via a Ugi-4CR four component reaction and subsequent macrocyclization of the resulting amides using intramol. SNAr reactions. [on SciFinder (R)] ...
Enantiomerically pure (-)-(1R,4R,5R,6S)- and (+)-(1S,4S,5S,6R)-7-(tert-butoxycarbonyl)-5,6-exo-isopropylidenedioxy-7- azabicyclo[2.2.1]hept-2-one ((-)-3 and (+)-3) have been obtained from the Diels-Alder adduct of N-(tert-butoxycarbonyl)pyrrole and 2-bromo ...
(2,6-Dichlorophenyl)- and (2,6-dibromophenyl)trialkylsilanes undergo hydrogen/metal interconversion preferentially at the 4- rather than 3-position. However, the organometallic species generated by such a "meta metalation" are thermodynamically less stab ...
Trifluoromethoxy-substituted anilines undergo hydrogen/lithium permutation ("metalation") with optional site selectivity depending on the N-protective group employed. N-tert-Butoxycarbonyl-2- and -4-(trifluoromethoxy)aniline react with tert-BuLi at the n ...
The synthesis of 46 derivatives of (2R,3R,4S)-2-(aminomethyl)pyrrolidine-3,4-diol is reported (Scheme I and Fig. 3), and their inhibitory activities toward alpha-mannosidases from jack bean (B) and almonds (A) are evaluated (Table). ne most-potent inhibito ...
It was possible to functionalize the three fluorobenzyl alcs. and the three 2-(fluorophenyl)ethanols by metalation and subsequent carboxylation, the prototype electrophilic trapping reaction. Triisopropylsilyl (TIPS) outperformed methoxymethyl (MOM) as an ...
Modern organometallic methods enable the regioflexible conversion of simple heterocyclic starting materials into families of isomers and congeners. Depending on the choice of the reagent, 1-methyl-5-(trifluoromethyl)pyrazole undergoes deprotonation and sub ...
This contribution describes the synthesis and ring-opening (co)polymerization of several L-lysine N-carboxyanhydrides (NCAs) that contain labile protective groups at the ε-NH2 position. Four of the following L-lysine NCAs were investigated: Nε-trifluoroace ...
