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Catalytic Enantioselective Synthesis of Tetrahydroisoquinolines and Their Analogues Bearing a C4 Stereocenter: Formal Synthesis of (+)-(8S,13R)-Cyclocelabenzine
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Abstract
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 oxetane-tethered benzaldehydes, amines, and the dimethyl ester derivative
of the Hantzsch ester (see scheme). This transformation can be used to prepare the
spermidine alkaloid (+)-(8S,13R)-cyclocelabenzine.
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Most cited references55
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Chiral Phosphoric Acids as Versatile Catalysts for Enantioselective Transformations
Masahiro Terada (2010)
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Binaphthol-derived phosphoric acid as a versatile catalyst for enantioselective carbon–carbon bond forming reactions
Masahiro Terada (2008)