111881-64-2Relevant articles and documents
Metal-Free C-C/C-N/C-C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[ b]indolines
Lázaro-Milla, Carlos,Yanai, Hikaru,Almendros, Pedro
, p. 2921 - 2926 (2021)
A bis(triflyl)ethylation [triflyl = (trifluoromethyl)sulfonyl] inserted into a sequential cyclization cascade resulted in the direct formation of gem-bis(triflyl)ated cyclopenta[b]indolines from anilide-derived allenols and alkenols. This catalyst- and irradiation-free sequence facilitated the efficient preparation of functionalized tricyclic indoline cores bearing two contiguous stereocenters. The formed cyclopenta[b]indolines can be easily transformed into a wide variety of triflylated indolines, including the tetracycle ring system found in polyveoline.
Catalytic Asymmetric Construction of the Tryptanthrin Skeleton via an Enantioselective Decarboxylative [4 + 2] Cyclization
Mei, Guang-Jian,Bian, Chen-Yu,Li, Guo-Hao,Xu, Shao-Li,Zheng, Wen-Qin,Shi, Feng
supporting information, p. 3219 - 3222 (2017/06/23)
The first catalytic asymmetric construction of the tryptanthrin skeleton has been established, taking advantage of a palladium(0)/chiral ligand-catalyzed enantioselective decarboxylative [4 + 2] cyclization of vinyl benzoxazinanones with isatins. This rea
A convenient allenoate-based synthesis of 2-quinolin-2-yl malonates and β-ketoesters
Selig, Philipp,Raven, William
, p. 5192 - 5195 (2014/12/11)
N-Protected o-aminobenzaldehydes smoothly react with α,γ-dialkylallenoates under Bronsted basic conditions to yield 2,3-disubstituted quinolines. This three-step reaction cascade of Michael addition, aldol condensation, and 1,3-N → C rearrangement uses the complete protecting group as a building block in a highly efficient C,C-bond formation of a new all-carbon quaternary center. Carbamate protected substrates (N-Boc, N-Cbz, N-Alloc) thus give 2-quinolin-2-yl-malonates, while amide protected substrates (N-Ac, N-Bz) afford 2-quinolin-2-yl-β-ketoesters in high yields.
