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- W2289923783 endingPage "2163" @default.
- W2289923783 startingPage "2139" @default.
- W2289923783 abstract "A range of enantiopure 1,2,3,4-tetrahydroisoquinolines have been prepared directly from α-hydroxy-β-amino esters. Activation of the α-hydroxy group upon treatment with Tf2O and 2,6-di-tert-butyl-4-methylpyridine promotes aziridinium formation, which is then followed by rupture of the C(3)–N bond and Friedel–Crafts alkylation-type cyclisation of an N-benzyl moiety onto the resultant benzylic carbenium ion. The nature of the N-protecting group was varied and it was found that superior yields were obtained for reactions employing two benzylic groups. In the cases where two different N-benzyl groups were used, the regioselectivity resulting from competitive cyclisation of either N-benzyl group was addressed by the introduction of a p-trifluoromethyl group on one of the N-benzyl moieties, which retarded the rate of cyclisation via this electron poor aryl ring. This methodology was employed in the asymmetric synthesis of a range of enantiopure 1,2,3,4-tetrahydroisoquinolines, which were isolated in good yields as single diastereoisomers." @default.
- W2289923783 created "2016-06-24" @default.
- W2289923783 creator A5002441008 @default.
- W2289923783 creator A5021159543 @default.
- W2289923783 creator A5042218147 @default.
- W2289923783 creator A5065969896 @default.
- W2289923783 creator A5088382037 @default.
- W2289923783 creator A5090924924 @default.
- W2289923783 date "2016-04-01" @default.
- W2289923783 modified "2023-10-12" @default.
- W2289923783 title "Trading N and O. Part 3: Synthesis of 1,2,3,4-tetrahydroisoquinolines from α-hydroxy-β-amino esters" @default.
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