Synthesis of (−)-kainic acid using chiral lithium amides in an asymmetric dearomatizing cyclization

A study on the metalation of fluorinated phenyl benzyl ethers

“…Flurbiprofen (anti-inflammatory) was synthesized from 3-fluorotoluene via ortho and benzylic lithiation as key steps. 1 Snieckus synthesized ochratoxine (a metabolite of Aspergillus ochraceus and Penicillium viridicatum) from 4-chlorophenol using a series of directed ortho lithiations. 2 The other examples involve the ortho lithiation of 1,2-methylenedioxybenzoic acid to obtain corydalic acid methyl ester, 3 ortho lithiation of 2-chloropyridine in the synthesis of the antibiotic atpenin B, 4 benzylic metalation of p-xylene in the synthesis of ibuprofen 5 and (−)-sparteine assisted enantioselective lithiation of carbamate derivative of n-dodecanol.…”

Diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative

“…The N- pivaloyl group on 11 was converted to the Boc group, because ruthenium oxidation did not proceed on using the pivaloyl-protected substrate 11 . The phenyl group was oxidized to the carboxylic acid by using ruthenium trichloride [15–16], and the benzylation of the carboxyl group yielded the pyroglutamic acid derivative 13 as a single stereoisomer (Scheme 3). …”

On the Preparation and Determination of Configurational Stability of Chiral Thio- and Bromo[D1]methyllithiums

“…11 Thus, sulfur- and selenium-substituted alkyllithiums are configurationally less stable than the oxygen-substituted ones. 12 The same is true for phosphorus versus nitrogen and silicon versus carbon-substituted chiral methyllithiums. 13 Investigations of the structure of many α-heteroatom-substituted alkyllithiums 14 and mechanistic 15 studies on the enantiomerization of α-thioalkyllithiums have been performed.…”