Stereoselective synthesis of 1, 3-disubstituted dihydroisoquinolines vial-phenylalanine-derived dihydroisoquinoline N-oxides. Issue 38 (19th September 2018)

• Record Type: Journal Article
• Authors: Flores-Ferrándiz, Jesús; Carter, Nicholas; González-Soria, Maria José; Wasinska, Malgorzata; Gill, Daniel; Maciá, Beatriz; Caprio, Vittorio
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 38(2018)
• Page Start: 6961
• Page End: 6968
• Publication Date: 2018-09-19
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob02007h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Addition of Grignard reagents and alkenes to readily available ( S )-3-(hydroxymethyl)-3, 4-dihydroisoquinoline-2-oxide allow the highly stereoselective synthesis of a range of 1, 3-disubstituted tetrahydroisoquinolines. Abstract : The preparation of chiral pool-derived nitrone3 and its use in the protecting-group free, stereoselective synthesis of a range of 1, 3-disubstituted tetrahydroisoquinolines is described. Grignard reagent additions to nitrone3 yielded trans -1, 3-disubstituted N -hydroxytetrahydroisoquinolines6 with good levels of selectivity, while 1, 3-dipolar cycloadditions to this nitrone provided access to 3-(2-hydroxyalkyl)isoquinolines12 as single diastereomers.