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- W1964558777 abstract "The 1,2,3,4-tetrahydro-N-pivaloyl-isoquinoline-3-carboxylic acids 1d, 2d, and 3d, derived from (R)- or (S)-phenylalanine, (S)-dopa, and (S)-α-methyldopa, respectively, are doubly deprotonated with (tert-butyl)lithium in THF and alkylated at the 1-position (products 5–10). The major diastereoisomers formed are the result of electrophilic attack from the face opposite to the carboxylate group (rel. topicity ul-1,3). Even the addition to benzaldehyd (→7,8) is highly stereoselective (one of four diastereoisomers is formed exclusively (300-MHz 1H-NMR analysis)), if MgBr2 etherate is added prior to the electrophile. Some of the obtained amino-acid derivatives are decarboxylated by anodic oxidation in MeOH (→11, 12, 17) and NaBH3CN reduction, and converted to the known 1-methyl- and 1-benzyltetrahydroisoquinolines (15, 16) of > 95% ee as well as to the phthalide isoquinoline alkaloid (+)-corlumine of ≥80% ee. The synthetic approach described here is compared with other methods of synthesizing enantiomerically pure 1-substituted tetrahydroisoquinolines (and thus an important group of alkaloids, Scheme 1)." @default.
- W1964558777 created "2016-06-24" @default.
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- W1964558777 date "1987-11-04" @default.
- W1964558777 modified "2023-09-26" @default.
- W1964558777 title "EPC-Synthesis of Tetrahydroisoquinolines by Diastereoselective Alkylation at the 1-Position of Phenylalanine-Derived Precursors. Synthesis of the Alkaloid (+)-Corlumine" @default.
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- W1964558777 doi "https://doi.org/10.1002/hlca.19870700729" @default.
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