Asymmetric Synthesis of 4-Hydroxy-3-phenyltetrahydroisoquinoline Derivatives Using Enantiopure Sulfinimines (N-Sulfinyl Imines) was written by Davis, Franklin A.;Andemichael, Yemane W.. And the article was included in Journal of Organic Chemistry in 1999.Recommanded Product: 4741-62-2 This article mentions the following:
Addition of lateral lithiated amides and phthalide anions to enantiopure sulfinimines (N-sulfinyl imines) represents a new approach for the asym. synthesis of 3-substituted isoquinolones and 3-substituted 4-hydroxy isoquinolones, resp., important chiral building blocks for isoquinoline alkaloid synthesis. In one example (-)-3-phenylisoquinolone was prepared in >95% ee by treatment of amide ion I with sulfinimine (S)-(+)-II and subsequent deprotection of the N-sulfinyl auxiliary and cyclization. Oxaziridine-mediated hydroxylation of the anion of afforded 4-hydroxy isoquinolone, which was transformed into the tetrahydroisoquinoline (III). In another approach III was prepared more directly by addition of a phthalide ion to II, creating the two stereogenic centers simultaneously. The selectivity proved to be highly counterion dependent. In the experiment, the researchers used many compounds, for example, 5-Methoxyisobenzofuran-1(3H)-one (cas: 4741-62-2Recommanded Product: 4741-62-2).
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Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem