38256-56-3Relevant articles and documents
Synthesis of (+)-(R)-methyl 2-aminotetraline-2-carboxylate: The hydroxypinanone method versus the bislactim method
Solladie-Cavallo, Arlette,Martin-Cabrejas, Luisa M.,Caravatti, Giorgio,Lang, Marc
, p. 967 - 969 (2001)
The methyl ester of 2-aminotetraline-2-carboxylic acid (Atc-OMe), an important residue for modified peptides, could only be synthesized from the Schoellkopf bislactim method, the hydroxypinanone method leading, during the second step, to elimination inste
Sulfones as Synthetic Linchpins: Transition-Metal-Free sp3–sp2 and sp2–sp2 Cross-Couplings Between Geminal Bis(sulfones) and Organolithium Compounds
Trost, Barry M.,Kalnmals, Christopher A.
supporting information, p. 9066 - 9074 (2018/06/29)
A valuable umpolung strategy that highlights the ambiphilic nature of the bis(phenylsulfonyl)methyl synthon and demonstrates its utility as a synthetic linchpin is reported. Although the bis(phenylsulfonyl)methyl group is typically introduced as an sp3-carbon nucleophile, it is demonstrated that it can also function as an effective sp2-carbon electrophile in the presence of organolithium nucleophiles. Alkyl- and aryllithiums couple with the central carbon of the bis(phenylsulfonyl)methyl unit to ultimately generate trisubstituted alkenes, comprising formal sp3–sp2 and sp2–sp2 cross-couplings between organolithium reagents and bis(sulfones). This process occurs almost instantaneously at ?78 °C in the absence of any transition metals. By developing this curious transformation, it has been demonstrated that bis(phenylsulfonyl)methane is a valuable synthetic linchpin, which can undergo two C?C bond-forming processes as an sp3-nucleophile, followed by a third C?C bond-forming reaction as an effective sp2-electrophile. This discovery significantly enhances the utility of this ubiquitous, but underutilized, linker group.
A new synthesis of indoles via intramolecular cyclization of ?-alkynyl N,N-dialkylanilines promoted by KOt-Bu/DMSO
Chen, Yan-Yan,Chen, Jia-Hua,Zhang, Niu-Niu,Ye, Lin-Miao,Zhang, Xue-Jing,Yan, Ming
supporting information, p. 478 - 481 (2015/03/05)
2-Aryl indoles could be prepared in excellent yields via the intramolecular cyclization of ?-alkynyl N,N-dialkylanilines. The reaction is efficiently promoted by the catalytic amount of KOt-Bu in DMSO at room temperature. A reaction mechanism involving α-