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2.1.5.2.2 Biocatalyzed Synthesis of 1-Substituted Tetrahydroisoquinolines

DOI: 10.1055/sos-SD-215-00081

Ilari, A.; Bonamore, A.; Boffi, A.Science of Synthesis: Biocatalysis in Organic Synthesis, (20152166.

The stereoselectivity of the TfNCS-catalyzed reaction to yield S-configured products has been thus probed toward a number of aldehyde substrates 10 including phenylacetaldehydes substituted with various electron-withdrawing or electron-donating groups, heteroaromatic moieties, aromatic bicyclics, aliphatic (hetero)cycles, and aliphatic open-chained compounds (Scheme 6).[‌17‌] All benzylic aldehydes are turned over at a comparable rate whereas aliphatic compounds and unsubstituted phenylacetaldehyde are processed at a slower rate. Small aldehydes, such as acetaldehyde and propanal, as well as α-substituted aldehydes and benzaldehyde, are not recognized as substrates. General procedures for the synthesis of the aromatic- and aliphatic-substituted acetaldehydes comprise oxidation of the corresponding alcohols 9 by chemical methods that require a final chromatographic purification step and the use of dichloromethane as solvent. TfNCS-catalyzed reactions between dopamine (1) and aldehydes 10 were carried out on analytical scale and were analyzed by quantitative chromatographic methods (HPLC-UV and LC/MS). No total yields of isolated products 11 were reported.

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