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.

  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},
  volume={17 17},
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)
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Super acid-induced Pummerer-type cyclization reaction: improvement in the synthesis of chiral 1,3-dimethyl-1,2,3,4-tetrahydroisoquinolines.
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Theoretical Study of 1-Methoxy-2-sulfanylethan-1-yl Cation: Insight into Intermediates in Glycosidation Reactions
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High 1,3-Asymmetric Induction in Addition of Allylic Tin Reagents to Chiral 3-Substituted 3,4-Dihydroisoquinolines Activated by Acyl Chlorides
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