A synthetic route to highly substituted 1,2,3,4-tetrahydroisoquinolines via Yb(OTf)3 -catalyzed diastereoselective ring opening of bridged oxazolidines: asymmetric synthesis of 2-azapodophyllotoxin.

@article{Srivastava2011ASR,
  title={A synthetic route to highly substituted 1,2,3,4-tetrahydroisoquinolines via Yb(OTf)3 -catalyzed diastereoselective ring opening of bridged oxazolidines: asymmetric synthesis of 2-azapodophyllotoxin.},
  author={Ajay Kumar Srivastava and Minseob Koh and Seung Bum Park},
  journal={Chemistry},
  year={2011},
  volume={17 17},
  pages={
          4905-13
        }
}
We herein report a robust and efficient synthetic route to highly functionalized enantiopure 1,2,3,4-tetrahydroisoquinolines (THIQs) from Garner aldehyde. We utilized the inherent chirality of Garner aldehyde through 1,2- and 1,3-/1,4-asymmetric inductions iteratively to obtain 1,2,3,4-tetrasubstitued THIQs using rigid and isolable bridged oxazolidines without any external chiral sources. All possible stereoisomers of bridged oxazoliodines were efficiently synthesized from L- and D-Garner… 
17 Citations
Stereoselective synthesis of functionalized 1,2,3,4-tetrahydroisoquinolines (THIQs) via highly diastereoselective Ugi three-component reactions (U3CRs) with chiral 3,4-dihydroisoquinolines (DHIQs)
A highly diastereoselective Ugi three-component reaction (U3CR) involving chiral 3,4-dihydroisoquinolines (DHIQs), isocyanides and carboxylic acids has been developed to synthesize enantiopure
Catalytic enantioselective synthesis of tetrahydroisoquinolines and their analogues bearing a C4 stereocenter: formal synthesis of (+)-(8S,13R)-cyclocelabenzine.
A one-pot wonder: 1,2,3,4-Tetrahydroisoquinolines with a C4 stereocenter can be formed by using a one-pot multicomponent chiral phosphoric acid catalyzed transformation of a mixture of
Lewis acid-catalyzed [3+3] cycloadditions of donor‒acceptor aziridines with N,N-dialkyl-3-vinylanilines via carbon-carbon bond cleavage
Abstract A Lewis acid-catalyzed [3 + 3] cycloaddition reaction of donor‒acceptor aziridines with N,N-dialkyl-3-vinylanilines has been developed for the stereoselective synthesis of
Cyclic Imines in Ugi and Ugi-Type Reactions.
TLDR
This review includes all research articles related to Ugi reactions based on the cyclic imines to the year 2020, and will be useful to chemists in designing novel synthetic routes for the synthesis of individual and combinatorial libraries of natural products and drug-like compounds.
Design, synthesis and biological evaluations of chirally pure 1,2,3,4-tertrahydroisoquinoline analogs as anti-cancer agents.
TLDR
A series of fifteen chiral 1,2,3,4-tetrahydroisoquinoline derivatives have been synthesized and their antiproliferative properties have been studied, revealing that these compounds induced cell cycle arrest at G2/M phase and effectively inhibit microtubule assembly formation in DU-145.
Construction of Highly Functionalized Piperazinones via post-Ugi Cyclization and Diastereoselective Nucleophilic Addition.
TLDR
A novel method for the generation of uniquely functionalized piperazinones by utilizing post-Ugi functionalization has been described and was employed to synthesize trans-dragmacidine C and praziquantel like molecules.
Spectroscopic and X-ray crystallographic evidence for electrostatic effects in 4-substituted cyclohexanone-derived hydrazones, imines, and corresponding salts.
TLDR
The axial conformer of several 4-substituted cyclohexanone hydrazone salts was found to predominate in solution and X-ray crystallography demonstrated that the axial configuration of a pendant benzyloxy group is the preferred conformation of an iminium ion in the solid state.
Ytterbium(III) triflate
This article has no abstract. Keywords: conjugate addition; cross-aldol reactions; allylation of aldehydes; isomerization of silyl ketene acetals; Friedel–Crafts acylation; cleavage of
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